113165PathwayBloch Pathway (Cholesterol Biosynthesis) The Bloch pathway, named after Konrad Bloch, is the pathway following the mevalonate pathway occurring within the cell to complete cholesterol biosynthesis. Cholesterol is a necessary metabolite that helps create many essential hormones within the human body. This pathway, combined with the mevalonate pathway is one of two ways to biosynthesize cholesterol; the Kandutsch-Russell pathway is an alternative pathway that uses different compounds than the Bloch Pathway beginning after lanosterol. The first three reactions occur in the endoplasmic reticulum. Lanosterol, a compound created through the mevalonate pathway, binds with the enzyme lanosterol 14-alpha demethylase to become 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol. Moving to the next reaction, 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol utilizes the enzyme lanosterol 14-alpha demethylase to create 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol. Lanosterol 14-alpha demethylase is used one last time in this pathway, converting 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol into 4,4-dimethyl-5a-cholesta-8,14,24-trien-3b-ol. Entering the inner nuclear membrane, 4,4-dimethyl-5a-cholesta-8,14,24-trien-3b-ol is catalyzed by a lamin B receptor to create 4,4-dimethyl-5a-cholesta-8,24-dien-3-b-ol. Entering the endoplasmic reticulum membrane, 4,4-dimethyl-5a-cholesta-8,24-dien-3-b-ol, with the help of methyl monooxygenase 1 is converted to 4a-hydroxymethyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol. The enzyme methyl monooxygenase 1 uses 4a-hydroxymethyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol to produce 4a-formyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol. This reaction is repeated once more, using 4a-formyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol and methyl monooxygenase 1 to create 4a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol. Briefly entering the endoplasmic reticulum, 4a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol then uses sterol-4-alpha-carboxylate-3-dehyrogenase to catalyze into 3-keto-4-methylzymosterol. Back in the endoplasmic reticulum membrane, where the pathway will continue on for the remaining reactions, 3-keto-4-methylzymosterol combines with 3-keto-steroid reductase to create 4a-methylzymosterol. 4a-Methylzymosterol joins the enzyme methylsterol monooxgenase 1 to result in 4a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol. 4a-Hydroxymethyl-5a-cholesta-8,24-dien-3b-ol uses methylsterol monooxygenase 1 to convert to 4a-formyl-5a-cholesta-8,24-dien-3b-ol. 4a-Formyl-5a-cholesta-8,24-dien-3b-ol proceeds to use the same enzyme used in the previous reaction: methylsterol monooxygenase 1, to catalyze into 4a-carboxy-5a-cholesta-8,24-dien-3b-ol. Sterol-4-alpha-carboxylate-3-dehydrogenase is used alongside 4a-carboxy-5a-cholesta-8,24-dien-3b-ol to produce 5a-cholesta-8,24-dien-3-one (also known as zymosterone). Zymosterone (5a-cholesta-8,24-dien-3-one) teams up with 3-keto-steroid reductase to create zymosterol. Zymosterol proceeds to use the enzyme 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase to catalyze into 5a-cholesta-7,24-dien-3b-ol. The compound 5a-cholesta-7,24-dien-3b-ol then joins lathosterol oxidase to convert to 7-dehydrodesmosterol. 7-Dehydrodesmosterol and the enzyme 7-dehydrocholesterol reductase come together to create desmosterol. This brings the pathway to the final reaction, where desmosterol combines with delta(24)-sterol reductase to finally convert to cholesterol. MetabolicPW122325CenterPathwayVisualizationContext12260145006100#000099PathwayVisualization113028113165Bloch Pathway (Cholesterol Biosynthesis) The Bloch pathway, named after Konrad Bloch, is the pathway following the mevalonate pathway occurring within the cell to complete cholesterol biosynthesis. Cholesterol is a necessary metabolite that helps create many essential hormones within the human body. This pathway, combined with the mevalonate pathway is one of two ways to biosynthesize cholesterol; the Kandutsch-Russell pathway is an alternative pathway that uses different compounds than the Bloch Pathway beginning after lanosterol. The first three reactions occur in the endoplasmic reticulum. Lanosterol, a compound created through the mevalonate pathway, binds with the enzyme lanosterol 14-alpha demethylase to become 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol. Moving to the next reaction, 4,4-dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol utilizes the enzyme lanosterol 14-alpha demethylase to create 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol. Lanosterol 14-alpha demethylase is used one last time in this pathway, converting 4,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol into 4,4-dimethyl-5a-cholesta-8,14,24-trien-3b-ol. Entering the inner nuclear membrane, 4,4-dimethyl-5a-cholesta-8,14,24-trien-3b-ol is catalyzed by a lamin B receptor to create 4,4-dimethyl-5a-cholesta-8,24-dien-3-b-ol. Entering the endoplasmic reticulum membrane, 4,4-dimethyl-5a-cholesta-8,24-dien-3-b-ol, with the help of methyl monooxygenase 1 is converted to 4a-hydroxymethyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol. The enzyme methyl monooxygenase 1 uses 4a-hydroxymethyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol to produce 4a-formyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol. This reaction is repeated once more, using 4a-formyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol and methyl monooxygenase 1 to create 4a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol. Briefly entering the endoplasmic reticulum, 4a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol then uses sterol-4-alpha-carboxylate-3-dehyrogenase to catalyze into 3-keto-4-methylzymosterol. Back in the endoplasmic reticulum membrane, where the pathway will continue on for the remaining reactions, 3-keto-4-methylzymosterol combines with 3-keto-steroid reductase to create 4a-methylzymosterol. 4a-Methylzymosterol joins the enzyme methylsterol monooxgenase 1 to result in 4a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol. 4a-Hydroxymethyl-5a-cholesta-8,24-dien-3b-ol uses methylsterol monooxygenase 1 to convert to 4a-formyl-5a-cholesta-8,24-dien-3b-ol. 4a-Formyl-5a-cholesta-8,24-dien-3b-ol proceeds to use the same enzyme used in the previous reaction: methylsterol monooxygenase 1, to catalyze into 4a-carboxy-5a-cholesta-8,24-dien-3b-ol. Sterol-4-alpha-carboxylate-3-dehydrogenase is used alongside 4a-carboxy-5a-cholesta-8,24-dien-3b-ol to produce 5a-cholesta-8,24-dien-3-one (also known as zymosterone). Zymosterone (5a-cholesta-8,24-dien-3-one) teams up with 3-keto-steroid reductase to create zymosterol. Zymosterol proceeds to use the enzyme 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase to catalyze into 5a-cholesta-7,24-dien-3b-ol. The compound 5a-cholesta-7,24-dien-3b-ol then joins lathosterol oxidase to convert to 7-dehydrodesmosterol. 7-Dehydrodesmosterol and the enzyme 7-dehydrocholesterol reductase come together to create desmosterol. This brings the pathway to the final reaction, where desmosterol combines with delta(24)-sterol reductase to finally convert to cholesterol. Metabolic1109692113163SubPathway27973723696639Sharpe LJ, Brown AJ: Controlling cholesterol synthesis beyond 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCR). J Biol Chem. 2013 Jun 28;288(26):18707-15. doi: 10.1074/jbc.R113.479808. Epub 2013 May 21.113165Pathway27973824095826Zerenturk EJ, Sharpe LJ, Ikonen E, Brown AJ: Desmosterol and DHCR24: unexpected new directions for a terminal step in cholesterol synthesis. Prog Lipid Res. 2013 Oct;52(4):666-80. doi: 10.1016/j.plipres.2013.09.002. Epub 2013 Oct 2.113165Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001824CardiomyocyteCL:00007463NeuronCL:00005407Epithelial CellCL:000006612AstrocyteCL:00001271Homo sapiens9606EukaryoteHuman18Saccharomyces cerevisiae4932EukaryoteYeast12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia4202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum13Endoplasmic ReticulumGO:00057835CytoplasmGO:00057371CytosolGO:00058297Endoplasmic Reticulum MembraneGO:00057896LysosomeGO:00057644PeroxisomeGO:000577710Cell MembraneGO:000588616Lysosomal LumenGO:00432022MitochondrionGO:000573911Extracellular SpaceGO:00056153Mitochondrial MatrixGO:000575918Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575835ChloroplastGO:000950736MembraneGO:001602012Mitochondrial Inner MembraneGO:000574331Periplasmic SpaceGO:000562025Golgi ApparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563453Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259732Inner MembraneGO:00702588Smooth Endoplasmic Reticulum GO:000579019Sarcoplasmic ReticulumGO:001652939Mitochondrial membraneGO:00319662Endothelium BTO:00003931LiverBTO:00007597294Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273106KidneyBTO:000067171824BrainBTO:000014289165cardiocyteBTO:00015393Sympathetic Nervous SystemBTO:000183216SkinBTO:000125315425181311PW_BS0000188511PW_BS0000081985181PW_BS0000241601181PW_BS00016021013181PW_BS0000241115121PW_BS000111122551PW_BS0001221355171PW_BS00013549711PW_BS0000499611PW_BS0000095411PW_BS00000516212PW_BS00001614101PW_BS0000142811611PW_BS0000283211PW_BS000003101711PW_BS000010311511PW_BS000031204111PW_BS00002015111PW_BS0000154311PW_BS000004331811PW_BS0000332111PW_BS0000022441011PW_BS000024221411PW_BS00002229111PW_BS000029422411PW_BS00004213121PW_BS0000131231751PW_BS0001231251351PW_BS000125126651PW_BS00012612711651PW_BS00012710813PW_BS0001081471241PW_BS00014715924PW_BS000159188118PW_BS0000241632181PW_BS0001632137181PW_BS00002421217181PW_BS000024151141PW_BS0001512164181PW_BS0000242156181PW_BS0000242111018PW_BS0000242253541PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS00002430013101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS000024171211PW_BS000017315123PW_BS00002429341PW_BS0000242941141PW_BS00002413412121PW_BS00013413013121PW_BS0001303317121PW_BS00002833217121PW_BS0000281136121PW_BS0001131151012PW_BS0001153344121PW_BS0000283361121PW_BS000028337116121PW_BS0000281122121PW_BS00011212915121PW_BS00012934141121PW_BS0000281141112PW_BS0001141333121PW_BS00013332914121PW_BS0000281321121PW_BS00013234524121PW_BS00002834318121PW_BS000028360410121PW_BS000028408451PW_BS000115405105PW_BS000115407251PW_BS0001154141551PW_BS000115409115PW_BS000115406351PW_BS0001154151851PW_BS000115124151PW_BS000124383751PW_BS00010043441051PW_BS000115429151PW_BS0001153821451PW_BS0001004182451PW_BS0001153841251PW_BS0001003744171PW_BS0000534436171PW_BS0001153761017PW_BS00005344717171PW_BS00011513613171PW_BS000136448116171PW_BS0001151192171PW_BS00011945015171PW_BS0001151371117PW_BS0001371203171PW_BS00012045118171PW_BS0001151181171PW_BS0001183987171PW_BS000113469410171PW_BS0001154641171PW_BS00011539914171PW_BS00011345424171PW_BS00011512112171PW_BS0001214824101PW_BS0001154781010PW_BS0001154831110PW_BS0001152975101PW_BS0000244793101PW_BS0001154812101PW_BS0001152991101PW_BS00002448414101PW_BS0001154957101PW_BS00011548924101PW_BS00011548012101PW_BS000115502461PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS000024205561PW_BS000024501361PW_BS0001155041861PW_BS000115206261PW_BS000024388161PW_BS00011251541061PW_BS0001153891461PW_BS0001123951361PW_BS000113390761PW_BS0001125062461PW_BS0001153911261PW_BS000112107313PW_BS0001073183123PW_BS000024541315PW_BS000054432511PW_BS00004360251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100943PW_BS000094103331PW_BS000103105113PW_BS000105110231PW_BS0001106131PW_BS000006140103PW_BS000140101531PW_BS00010114315191PW_BS0001431465191PW_BS000146951721PW_BS0000951553241PW_BS0001551572241PW_BS0001571613181PW_BS00016111PW_BS00000116611PW_BS0001661783211PW_BS0001781802211PW_BS00018015284PW_BS000152117131PW_BS00011721425181PW_BS000024222341PW_BS000024224241PW_BS0000241901118PW_BS00002417018PW_BS00017016212181PW_BS000162261115PW_BS0000262771218PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000243081011PW_BS0000243221231PW_BS000024253541PW_BS0000243331212PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS0000283683601PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154251355PW_BS0001154192551PW_BS000115436255PW_BS0001154461217PW_BS00011546013175PW_BS00011545525171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155072561PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS000549185321PW_BS0000241873118PW_BS000024219314PW_BS00002422014PW_BS0000241951318PW_BS0000243125231PW_BS0000243201123PW_BS00002432711125PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS0001094241155PW_BS00011545911175PW_BS00011588231202PW_BS00055288312021PW_BS000552167311PW_BS000167168321PW_BS000168788241113PW_BS00052459724112PW_BS000336111811PW_BS00001114117191PW_BS00014178811PW_BS0000783551914PW_BS000035193513PW_BS0000195811411PW_BS0000581021231PW_BS00010215612241PW_BS00015617912211PW_BS0001793583912PW_BS00002836912601PW_BS0000281861221PW_BS0000245311015PW_BS0000539731715PW_BS000569104716711PW_BS000577966LanosterolHMDB0001251Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide.(wikipedia).79-63-0C0172424698316521LANOSTEROL216175[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)CC30H50OInChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1CAHGCLMLTWQZNJ-BQNIITSRSA-N426.7174426.386166222FDB013802(3 beta)-lanosta-8,24-dien-3-ol;(3alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;(3beta)-lanosta-8,24-dien-3-ol;(3beta,5alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;4,4',14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol;Botalan base 138;Lanosta-8,24-dien-3-ol;Lanosta-8,24-dien-3beta-ol;Lanosta-8,24-dienol;Lanosterin;Lanosterol;Lanster;(3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol;(3b)-lanosta-8,24-dien-3-ol;(3β)-lanosta-8,24-dien-3-olPW_C000966Lastrol827181624873221987614160828621078931111121491122124049135140700491065OxygenHMDB0001377Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).7782-44-7C0000797715379CPD-6641952O=OO2InChI=1S/O2/c1-2MYMOFIZGZYHOMD-UHFFFAOYSA-N31.998831.989829244FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391891FMNH2HMDB0001142FMNH2 is the reduced form of flavin mononucleotide. It is a substrate of the enzyme FMN reductase (EC 1.5.1.29), an enzyme that catalyzes the chemical reaction FMNH2 + NAD(P)+ <=> FMN + NAD(P)H + H+. Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase. During a catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH•) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers.5666-16-0C0184744539516048FMNH2393046CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1C17H23N4O9PInChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/t11-,12+,14-/m0/s1YTNIXZGTHTVJBW-SCRDCRAPSA-N458.3597458.120264866FDB022449Fmnh2;Reduced fmn;Reduced flavin mononucleotide;1,5-dihydroriboflavin 5'-(dihydrogen phosphate);Flavin mononucleotide (reduced);Fmnh;1,5-dihydroriboflavin 5'-(dihydrogen phosphoric acid)PW_C000891FMNH211954225140701491046504,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol4,4-Dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol has the chemical formula C30H50O2, and an average molecular weight of 442.728. 4,4-Dimethyl-14α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol is involved in the Bloch Pathway (Cholesterol Biosynthesis) .22298935[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2(CO)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C30H50O2InChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3/t21-,22-,25+,26+,28-,29-,30-/m1/s1DWVYYKFZEDMMPU-PUXRVUTHSA-N442.728442.3810808530-hydroxylanosterol ;lanosta-8,24-dien-3β,30-diolPW_C104650DMHCOL1407024992Formic acidHMDB0000142Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.64-18-6C000581897100230751FORMATE278DB01942OC=OCH2O2InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYSA-N46.025446.005479308DBMET00489FDB012804Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600lPW_C000092Formate94689773162949194325314111534811266361077158205718620673252137616160828721011982151435223187696322578652132789343311206701221206974071214963831217511241232841351233021191240543981243021181257532971257724811264782991268214951276373881284263901420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-N18.015318.010564686FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851170Flavin MononucleotideHMDB0001520Flavin mononucleotide (FMN), or riboflavin-5?-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.146-17-8C0006164397617621FMN559060DB03247CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2C17H21N4O9PInChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1FVTCRASFADXXNN-SCRDCRAPSA-N456.3438456.104614802FDB001984Fmn;Flanin;Flavine mononucleotide;Flavol;Riboflavin;Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate;Riboflavin mononucleotide;Riboflavin monophosphate;Riboflavin phosphate;Riboflavin-5'-phosphate na;Riboflavin-5-phosphate;Riboflavine 5'-monophosphate;Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate;Riboflavine monophosphate;Riboflavine phosphate;Riboflavine-5'-phosphate;Vitamin b2 phosphate;Flavin mononucleotide;Riboflavin 5'-(dihydrogen phosphate)PW_C001170FlvnMnt539811901416922496131577210111900211123132257751911577590111787301321204334051204541221219291241230673761230881351244821181256982971261042991271902051273122091276863881407034940034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-N1.00791.007825032H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+215467087531578831848311162146326146454223149278017425022425442454710457618469470524110353271115353112562610856391075699100572010557421175963147603715560701576093161613015962321666483178660115266921016843188691018771001637168205719120674532197454220747222275252137532210755821275721607590170819522582181518243226841316284202249139195915524911915164120152811218128512246286122662871252122713257223133252941533030842329315423543184240132242405312424543207691229377136133772101347737233177804114779551327799032777991347783793457992913080019368803873108038830480722119938231249482338311055038811285594113280390115537398115539118115856336116205109119973406120193407120549122120593409121170424121171425122569418122615384122687125122758120123183135123218137123742459123743460125141454125188121125273136125359479125550481125730483125736297125809299126517495126717489126766480126823300126902501127213208128308506128361391128430395140692882140693883140699167140707168140715141407427881407435971407601851799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L616.487616.177297665FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911046514,4-dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol4,4-Dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol has the chemical formula C30H48O2, and an average molecular weight of 440.712. 4,4-Dimethyl-14α-formyl-5α-cholesta-8,24-dien-3β-ol is involved in the Bloch Pathway (Cholesterol Biosynthesis) .21121725[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C30H48O2InChI=1S/C30H48O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,19,21-22,25-26,32H,8,10-18H2,1-7H3/t21-,22-,25+,26+,28-,29-,30-/m1/s1PGGIMLIQOHYFIS-PUXRVUTHSA-N440.712440.365430786oxolanosterolPW_C104651DFCDol140704491046524,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol4,4-Dimethyl-5α-cholesta-8,14,24-trien-3β-ol has the chemical formula C29H46O, and an average molecular weight of 410.6749. 4,4-Dimethyl-5α-cholesta-8,14,24-trien-3β-ol is involved in the Bloch Pathway (Cholesterol Biosynthesis) .443212C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3C29H46OInChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1LFQXEZVYNCBVDO-PBJLWWPKSA-N410.6749410.3548660944,4-dimethyl-cholesta-8,14,24-trienolPW_C104652DmCTBol14070549146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N745.4209745.091102105FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH185819037781079658211883721609291615494687314793144797145310111578910859721476128159627135677911770681887103163715420572051607315213734521075592127591170819422582191518421224118121981189321112006222121501641224528612596226126482494234331543746322769112937716613277385331773943327746013077504112775111157762333680712119113164941201054071204254051204521221206161231211411251212754291214021241214833831230593761230861351232414471237121361238464641239611181240413981254724811256962971262142991265294951270092061275723881281013901407061689944,4-Dimethyl-5a-cholesta-8,24-dien-3-b-olHMDB00012864,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol (14-demethyllanosterol) is an intermediate in sterol biosynthesis. In particular, it is an intermediate in the conversion of lanosterol to zymosterol. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is a substrate for C-4 methyl sterol oxidase, NAD(P)-dependent steroid dehydrogenase, Cytochrome P450 51A1 and Delta(14)-sterol reductase.7448-02-4C05108509900811836444-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET25994967[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12CC29H48OInChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1CHGIKSSZNBCNDW-GKBRUXRCSA-N412.6908412.370516158FDB022534(3beta,5alpha)-4,4-dimethylcholesta-8,24-dien-3-ol;14-demethyllanosterol;4,4-dimethyl-5 alpha -cholesta-8,24-dien-3 beta -ol;4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol;4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol;4,4-dimethyl-5a-cholesta-8,24-dien-3b-ol;4,4-dimethyl-5alpha -cholesta-8,24-dien-3-beta -ol;4,4-dimethyl-5alpha-cholest-7-en-3beta-ol;4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol;4,4-dimethyl-8,24-cholestadienol;4,4-dimethylzymosterolPW_C00099444Dcdol16314973272137618160828821078935331121498383124056398140708168143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N743.405743.075452041FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390140709168544Fe2+HMDB0000692Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.15438-31-0C148182728429033Ferric-Hydroxamate-Complexes25394DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133FDB016251Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)PW_C000544Fe2+398196413678316922070981777270411637052160120602251214315177179132777401127775112977760341777821111205444071205574141205701221217651241231781191231914501232041351243161181261432991261854811276503881407104914071618104654 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol has the chemical formula C29H48O2, and an average molecular weight of 428.701. 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol is involved in the Bloch Pathway (Cholesterol Biosynthesis) .2229893687289C[C@H](CCC=C(C)C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO)[C@@H]1CC3C29H48O2InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h8,20,22-23,25-26,30-31H,7,9-18H2,1-6H3/t20-,22-,23+,25-,26+,27-,28-,29+/m1/s1LEUVIESGHNFBEK-WKYRUEGDSA-N428.701428.365430786PW_C104653hmmcdol140711498133Fe3+HMDB0012943Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.20074-52-6C148192993629034CPD-1013427815[Fe+3]FeInChI=1S/Fe/q+3VTLYFUHAOXGGBS-UHFFFAOYSA-N55.84555.934942133C14819Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))PW_C008133Fe3+1230312968142049199727042163118411601267515177431111774503317859911278721132120949407121013122121127383121593124123515119123578135123696398124151118125890481127351206127559388140718189794IronHMDB0015531Iron is a metallic element found in certain minerals, in nearly all soils, and in mineral waters. Iron is required for life. It exists in all living species, ranging from bacteria to humans. It can be found primarily in blood and it is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. In humans, iron is involved in several metabolic pathways, some of which include the rofecoxib pathway, magnesium salicylate action pathway, etodolac pathway, and diclofenac pathway. Iron is also involved in several metabolic disorders, some of which include adenine phosphoribosyltransferase deficiency (APRT), porphyria variegata (PV), adenylosuccinate lyase deficiency, and AICA-ribosiduria. The major activity of supplemental iron is in the prevention and treatment of iron-deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic, and cognition-enhancing activities. Iron can be found in a number of food items such as chinese water chestnut, hyssop, daikon radish, and peppermint, which makes it a potential biomarker for the consumption of these food products.7439-89-6C00023239251824822368DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133C0002326fe;Eisen;Fe;Fer;Ferrum;HierroPW_C009794Iron11388126651533216354931192943411873302131205622577683130779283367826113278409111784283347893833112083812212099240812125642912137112412150238312172712512342313512355737412382646412393011812406039812427813612582929712593248212604429912728220512739150212749638877224α-Formyl-4β-methyl-5α-cholesta-8,24-dien-3β-olHMDB00121674alpha-formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis I and in cholesterol biosynthesis III (via desmosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol or from the enzymatic oxidation of 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis II may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway. The sequence of reactions and the types of intermediates in cholesterol biosynthesis III (via desmosterol) may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway. In cholesterol biosynthesis I, 4alpha-formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol is an intermediate in the conversion of lanosterol to cholesterol. The enzymology of this multistep conversion was largely determined in rat liver and the human pathway is therefore inferred from this work. Indeed, the order of some of the reactions in this pathway may vary. The lanosterol-to-cholesterol conversion involves the oxidative removal of three methyl groups, reduction of double bonds, and migration of the lanosterol double bond to a new position in cholesterol. The reactions in the lanosterol pathway are catalyzed by membrane-bound enzymes. Human genes have been identified for all the enzymes in this pathway and human disorders of cholesterol metabolism have been associated with genetic defects in most of these enzymes.25200700CPD-4576CC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC3C29H46O2InChI=1S/C29H46O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h8,18,20,22-23,25-26,31H,7,9-17H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1GFGANDKVOKQAGH-AEWFMJFUSA-N426.6743426.3497807164a-formyl-4b-methyl-5a-cholesta-8,24-dien-3b-ol;4a-formyl-4beta-methyl-5a-cholesta-8,24-dien-3beta-ol;4alpha-formyl-4b-methyl-5alpha-cholesta-8,24-dien-3b-olPW_C007722fmcol140712499174a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-olHMDB0001181Intermediate in Cholesterol biosynthesis.C1580823724596CPD-457730792017C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=OC29H46O3InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1MYWAIWDQTCHPTH-YCIQJMEESA-N442.6737442.344695338FDB0224714a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol;4alpha-carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol;4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-olPW_C000917CMCDOL1407134929613-Keto-4-methylzymosterolHMDB00068383-Keto-4-methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG:C15816). It is the 8th to last step in the synthesis of vitamin D2 and is converted from 4-methtylzymosterol-carboxylate via the enzyme sterol-4alpha-carboxylate 3-dehydrogenase (decarboxylating) (EC:1.1.1.170). It is then converted to 4-methylzymosterol via the enzyme 3-keto steroid reductase (EC:1.1.1.270).C1581653477900505093CPD-4578C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3C28H44OInChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20?,22?,23?,24?,27-,28+/m1/s1DBPZYKHQDWKORQ-JQDPPCHWSA-N396.6484396.33921603FDB024112(5a)-4-methylcholesta-8,24-dien-3-one;(5alpha)-4-methylcholesta-8,24-dien-3-one;3-dehydro-4-methylzymosterol;3-keto-4-methylzymosterol;4-methyl-5a-cholesta-8,24-dien-3-one;4-methyl-5alpha-cholesta-8,24-dien-3-onePW_C0029613K4Mzol163749733221375292107623160789403311215043831240623981316Carbon dioxideHMDB0001967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-N44.009543.989829244DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO250812112044480135031864036773169520806511334316384917452255117314470528310353201115750108577110159681006026155607816164711786637107692219070171607035163706118871632057308198733321374612227530210821522582231519158249118492771190817012464226126882904262631543523318769942937712213377170132774703337773911277750129777633417807713478405356784273347894133179227130800083688067511980717135948363841132913911155491211199544061200891221201554071203644121205564141208334191209221241209914081212841251215053831227441201230114461231904501234184551234891181235563741238551361240633981253444791254602971255164811258244901258702991259314821262804801268875011270522061272775071273313881273905021407981859464a-MethylzymosterolHMDB00012174a-Methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG ID C05103). It is the 7th to last step in the synthesis of vitamin D2 and is converted from 3-keto-4-methtylzymosterol via the enzyme 3-keto steroid reductase [EC:1.1.1.270]. It is then converted to zymosterol. (KEGG).7448-03-5C051032221249519494-METHYL-824-CHOLESTADIENOL20036827[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)CC28H46OInChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1FOUJWBXBKVVHCJ-YIJYGBTNSA-N398.6642398.354866094FDB022496(3b,4a,5a)-4-methylcholesta-8,24-dien-3-ol;(3beta,4alpha,5alpha)-4-methylcholesta-8,24-dien-3-ol;(4s,5s)-4,10,13-trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol;4a-methyl-5a-cholesta-8,24-dien-3b-ol;4a-methylzymosterol;4alpha-methylzymosterol;4alpha-methyl-5alpha-cholesta-8,24-dien-3beta-ol;(3β,4α,5α)-4-methylcholesta-8,24-dien-3-olPW_C0009464aMzmol164049733421376251608291210789433311215073831240653981407141477274α-hydroxymethyl-5α-cholesta-8,24-dien-3β-olHMDB00121724Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from 4-alpha-methylzymosterol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.25202625CPD-4568CC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC3C28H46O2InChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,19,21-24,26,29-30H,6,8-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1ORZKEIGPXNMCHC-GYISYUOESA-N414.6636414.3497807164 alpha-hysroxymethyl-5 alpha-cholsta-8,24-dien-3 beta-ol;4-alpha-hysroxymethyl-5-alpha-cholsta-8,24-dien-3-beta-ol;4a-hydroxymethyl-5a-cholesta-8,24-dien-3b-olPW_C007727HmCDol140717189384a-Formyl-5a-cholesta-8,24-dien-3b-olHMDB00012034a-Formyl-5a-cholesta-8,24-dien-3b-ol is an intermediate in the biosynthesis of cholesterol, in a reaction catalyzed by the enzyme methylsterol monooxygenase (EC 1.14.13.72, 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,hydrogen-donor:oxygen oxidoreductase (hydroxylating)). (MetaCyc).656456CPD-4580570845CC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC3C28H44O2InChI=1S/C28H44O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3ZLQSSFNCEUGGJF-UHFFFAOYSA-N412.6478412.334130652FDB0224894alpha-formyl-5alpha-cholesta-8,24-dien-3beta -olPW_C00093845aFC3b140719181046554a-carboxy-5a-cholesta-8,24-dien-3b-ol4a-Carboxy-5a-cholesta-8,24-dien-3b-ol has the chemical formula C29H46O3, and an average molecular weight of 442.6737. 4a-Carboxy-5a-cholesta-8,24-dien-3b-ol is involved in the Bloch Pathway (Cholesterol Biosynthesis) .23724596C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=OC29H46O3InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1MYWAIWDQTCHPTH-YCIQJMEESA-N442.6737442.344695338PW_C1046554C5C8D314072018445795α-cholesta-8,24-dien-3-one5α-cholesta-8,24-dien-3-one, also known as zymosterone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5α-cholesta-8,24-dien-3-one is considered to be a sterol lipid molecule. 5α-cholesta-8,24-dien-3-one is considered to be a practically insoluble (in water) and relatively neutral molecule. 5α-cholesta-8,24-dien-3-one can be biosynthesized from 5alpha-cholestane. Outside of the human body, 5α-cholesta-8,24-dien-3-one can be found in a number of food items such as hickory nut, abalone, black cabbage, and cassava. This makes 5α-cholesta-8,24-dien-3-one a potential biomarker for the consumption of these food products.22298942[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C[C@]1([H])CC3)[C@H](C)CCC=C(C)CC27H42OInChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20+,23-,24+,26+,27-/m1/s1AUNLIRXIJAVBNM-ZSBATXSLSA-N382.6218382.323565966Zymosterone;5alpha-cholesta-8,24-dien-3-onePW_C0445795aChone763016082922101407214944580ZymosterolZymosterol intermediate 2, also known as zymostrol or 5a-cholesta-8,24-dien-3b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Zymosterol intermediate 2 exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Zymosterol intermediate 2 has been found throughout all human tissues, and has also been primarily detected in urine. Within the cell, zymosterol intermediate 2 is primarily located in the membrane (predicted from logP), endoplasmic reticulum and cytoplasm. In humans, zymosterol intermediate 2 is involved in the desmosterolosis pathway, the lovastatin action pathway, the rosuvastatin action pathway, and the pamidronate action pathway. Zymosterol intermediate 2 is also involved in several metabolic disorders, some of which include the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the child syndrome pathway, the hyper-igd syndrome pathway, and the wolman disease pathway. Outside of the human body, zymosterol intermediate 2 can be found in a number of food items such as white lupine, oil-seed camellia, sorrel, and devilfish. This makes zymosterol intermediate 2 a potential biomarker for the consumption of these food products.92746[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3C27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1CGSJXLIKVBJVRY-XTGBIJOFSA-N384.6377384.33921603Zymosterol;5alpha-cholesta-8,24-dien-3beta-ol;128-33-6;Delta8,24-cholestadien-3beta-ol;Cholesta-8,24-dien-3-ol #;ZymostrolPW_C044580Zymstol7538213763116082932101407221429655a-Cholesta-7,24-dien-3b-olHMDB00068425alpha-Cholesta-7,24-dien-3beta-ol is involved in the biosynthesis of steroids. 5alpha-Cholesta-7,24-dien-3beta-ol is reversibly converted to 5alpha-Cholest-7-en-3beta-ol by delta24-sterol reductase [EC:1.3.1.72]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to zymosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to 7-Dehydrodesmosterol. 5a-Cholesta-7,24-dien-3b-ol is a substrate for 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase.651-54-7C05439440670162905-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL389550[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1PKEPPDGGTSZLBL-FZAJRYLSSA-N384.6377384.33921603FDB0241155 alpha-cholesta-7,24-dien-3beta-ol;5alpha-cholesta-7,24-dien-3beta-olPW_C0029655CDBol16434973362137894633112151038312406839819897-DehydrodesmosterolHMDB00038967-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627, 17197219).1715-86-2C0510744055827910389458[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)CC27H42OInChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1RUSSPKPUXDSHNC-DDPQNLDTSA-N382.6218382.323565966FDB01278124-dehydroprovitamin d3;Cholesta-5,7,24-trien-3beta-ol;Cholesta-5,7,24-triene-3beta-ol;Cholesta-5,7,24-trien-3b-ol;Cholesta-5,7,24-trien-3β-ol;Cholesta-5,7,24-triene-3b-ol;Cholesta-5,7,24-triene-3β-olPW_C0019897-DHMOL16498733919875652137647160829821078949111121514122124072135140723491690DesmosterolHMDB0002719Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursor's 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203).313-04-2C0180243957717737CPD-4141388662[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1AVSXSVCZWQODGV-DPAQBDIFSA-N384.6377384.33921603FDB00537424-dehydrocholesterol;3beta-cholesta-5,24-dien-3-ol;Cholest-5,24-dien-3beta-ol;Cholesta-5,24-dien-3-ol;Cholesta-5,24-dien-3b-ol;Cholesta-5,24-dien-3beta-ol;Desmosterol;3b-cholesta-5,24-dien-3-ol;3β-cholesta-5,24-dien-3-ol;Cholesta-5,24-dien-3β-olPW_C001690Desmost16598734219875662107648160789521111215171221240751351407244947CholesterolHMDB0000067Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50% of the lipid in the membrane or 60-80% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginine (ADMA) in the endothelium since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with highly oxidized levels of LDL, pose a heightened risk factor for vascular disease. Chronically high levels of cholesterol are associated with at least five inborn errors of metabolism, including cerebrotendinous xanthomatosis, cholesteryl ester storage disease, congenital lipoid adrenal hyperplasia, hypercholesterolemia, and Zellweger syndrome. In chronically high levels, cholesterol can function as an atherogen (causes atherosclerosis and cardiovascular disease). Specifically, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease.57-88-5C00187599716113CHOLESTEROL5775DB04540[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1HVYWMOMLDIMFJA-DPAQBDIFSA-N386.6535386.354866094FDB013269(+)-ent-cholesterol;(-)-cholesterol;(20bfh)-cholest-5-en-3b-ol;(3b)-cholest-5-en-3-ol;(3beta)-cholest-5-en-3-ol;20-epi-cholesterol;20-iso-cholesterol;20bfh-cholest-5-en-3b-ol;3beta-hydroxycholest-5-ene;5-cholesten-3b-ol;5-cholesten-3beta-ol;5:6-cholesten-3-ol;5:6-cholesten-3beta-ol;Cholest-5-en-3-ol;Cholest-5-en-3b-ol;Cholest-5-en-3beta-ol;Cholesterin;Cholesterine;Cholesterol;Cholesterol base h;Cholesteryl alcohol;Cholestrin;Cholestrol;Cordulan;Dastar;Dusoline;Dusoran;Dythol;Epicholesterin;Epicholesterol;Fancol ch;Hydrocerin;Kathro;Lanol;Liquid crystal cn/9;Nimco cholesterol base h;Nimco cholesterol base no. 712;Super hartolan;TegolanPW_C000047Lanol82921658492330328402928451573412137567210764916077653336776851147895133178988112121516383121697429121731409121831407124074398124246464124282137124384119964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N785.5497785.157134455FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD9991145186819232164253176282882518840211881414894216122916224921335825362237232646023646883147411347581048816526810352851025335111549612655111275613118603015560541566082161611616263901647517864991796666107703916371752057321213746522274872239076224118182161188721511899211122962251232824912443151125192271259522612710291127202921302930113041302436233187708029377126133771521347750111377507112775181157754133477615132777263377805432978375345789303317922233679272358800123688003436980714119119958406119999384120051408120107407120432405120453122120490124121278429121298418121417382121489383122748120122776121122802374122823443123066376123087135123166448123849464123868454123976399124047398125348479125378480125429482125474481125697297125979489126107299126277484126891501126920391126968502126987207127011206127310209127432506127602388127840389140790185140799186259Lanosterol 14-alpha demethylaseQ16850Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
HMDBP00265CYP51A17q21.2U5168711.14.13.701630491357861814268753142688973142760104722637Lamin-B receptorQ14739
Anchors the lamina and the heterochromatin to the inner nuclear membrane.
LBR1135777168257Methylsterol monooxygenase 1Q15800HMDBP00263MSMO14q32-q34BC01065311.14.13.7216364913578018258Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingQ15738HMDBP00264NSDHLXq28BC00024511.1.1.170163949135787187933-keto-steroid reductaseP56937Responsible for the reduction of the keto group on the C-3 of sterols.
HMDBP00848HSD17B71q23AF16276111.1.1.270; 1.1.1.6216414913577914130Lathosterol oxidaseO75845Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
HMDBP00135SC5DL11q23.3BC01233311.14.21.61660495207-dehydrocholesterol reductaseQ9UBM7Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
HMDBP00548DHCR711q13.4AF06248111.3.1.21135782491688Delta(24)-sterol reductaseQ15392Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
HMDBP01935DHCR241p32.3AF39833711.3.1.72162749135785188923-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
HMDBP00949EBPXp11.23-p11.22BC00154915.3.3.5164449442Lanosterol 14-alpha demethylase1PW_P00044246525912131799112856Lamin-B Receptor1PW_P01285622615226371135778168444Methylsterol monooxygenase 11PW_P000444467257121497941445Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating1PW_P00044546825814463-keto-steroid reductase1PW_P0004464697931451Lathosterol oxidase1PW_P000451474130121597941128577-Dehydrodesmosterol reductase1PW_P01285722616520113578149441Delta(24)-sterol reductase1PW_P0004414641688121296414473-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase1PW_P0004474708921179296PW_R179296Right6764239661Compoundfalse67642410653Compoundfalse6764258913Compoundfalse6764261046501Compoundfalse676427921Compoundfalse67642814204Compoundfalse67642911703Compoundfalse676430400344Compoundfalse169201442179297PW_R179297Right6764311046501Compoundfalse67643210653Compoundfalse6764338913Compoundfalse6764341046511Compoundfalse676435921Compoundfalse67643614204Compoundfalse676437400344Compoundfalse67643811703Compoundfalse169202442179298PW_R179298Right6764391046511Compoundfalse67644010653Compoundfalse6764418913Compoundfalse6764421046521Compoundfalse676443921Compoundfalse67644414204Compoundfalse676445400344Compoundfalse67644611703Compoundfalse169203442179299PW_R179299Right6764471046521Compoundfalse6764481461Compoundfalse676449400341Compoundfalse6764509941Compoundfalse6764511431Compoundfalse16920412856179300PW_R179300Right6764529941Compoundfalse6764535446Compoundfalse676454400345Compoundfalse67645510653Compoundfalse6764561046541Compoundfalse67645781336Compoundfalse67645814204Compoundfalse169205444179301PW_R179301Right6764591046541Compoundfalse6764605446Compoundfalse676461400345Compoundfalse67646210653Compoundfalse67646377221Compoundfalse67646481336Compoundfalse67646514204Compoundfalse1692064441.14.13.72179302PW_R179302Right67646677221Compoundfalse6764675446Compoundfalse676468400345Compoundfalse67646910653Compoundfalse6764709171Compoundfalse67647181336Compoundfalse67647214204Compoundfalse169207444179303PW_R179303Right6764739171Compoundfalse6764741431Compoundfalse67647529611Compoundfalse67647613161Compoundfalse6764771461Compoundfalse169208445179304PW_R179304Right67647829611Compoundfalse6764791431Compoundfalse6764809461Compoundfalse6764811461Compoundfalse676482400341Compoundfalse169209446179305PW_R179305Right6764839461Compoundfalse6764845446Compoundfalse676485400345Compoundfalse67648610653Compoundfalse67648777271Compoundfalse67648881336Compoundfalse67648914204Compoundfalse169210444179306PW_R179306Right67649077271Compoundfalse6764915446Compoundfalse676492400345Compoundfalse67649310653Compoundfalse6764949381Compoundfalse67649581336Compoundfalse67649614204Compoundfalse169211444179307PW_R179307Right6764979381Compoundfalse6764985446Compoundfalse676499400345Compoundfalse67650010653Compoundfalse6765011046551Compoundfalse67650281336Compoundfalse67650314204Compoundfalse169212444179308PW_R179308Right6765041046551Compoundfalse6765051431Compoundfalse676506445791Compoundfalse6765071461Compoundfalse67650813161Compoundfalse169213445179309PW_R179309Right676509445791Compoundfalse6765101431Compoundfalse676511445801Compoundfalse676512400341Compoundfalse6765131461Compoundfalse169214446179310PW_R179310Right676514445801Compoundfalse67651529651Compoundfalse169215447179311PW_R179311Right67651629651Compoundfalse6765175442Compoundfalse676518400342Compoundfalse67651910651Compoundfalse67652019891Compoundfalse67652181332Compoundfalse67652214202Compoundfalse169216451179312PW_R179312Right67652319891Compoundfalse6765241431Compoundfalse67652516901Compoundfalse676526400341Compoundfalse6765271461Compoundfalse169217128571.3.1.21179313PW_R179313Right67652816901Compoundfalse6765291431Compoundfalse676530471Compoundfalse676531400341Compoundfalse6765321461Compoundfalse16921844126777999664982false135533510regular300280267780010654965false133680310regular787826778018914981false161074810regular20019026778021046504982false1365147310regular3002902677803924981false1615120810regular200190267780414204949false1341106810regular7878267780511704981false1230121110regular2001902677806400344955false1616107110regular787826778071799499false146094110regular10025267780810654965false1610194310regular787826778098914981false1230188810regular20019026778101046514982false1360263810regular3002902677811924981false1590222810regular200190267781214204949false1616247510regular78782677813400344955false1311247310regular7878267781411704981false1225223610regular20019026778151799499false1460212319regular10025267798210654965false1601303810regular787826779838914981false1225298310regular20019026779841046524982false1365394310regular3002802677985924981false1605330310regular200190267798614204949false1346352810regular78782677987400344955false1606352610regular7878267798811704981false1225330410regular20019026779891799499false1455320819regular10025267799014616862false1820415810regular503026779914003416855false1795393510regular7878267799299416882false2365394110regular300280267799314316861false2170417110regular503026779945444981false2615339810regular2001902677995400344955false2361340310regular7878267799610654965false2331351310regular787826779971046544982false2360257310regular300290267799881334981false2610300610regular200190267799914204949false2331306110regular787826780009794499false2460325019regular1002526780095444981false2195217810regular2001902678010400344955false2311243310regular7878267801110654965false2611227310regular7878267801277224982false2355144810regular300290267801381334981fal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615 C1507 655 1510 922 1510 951 5false183656596M1414 842 C1457 842 1508 861 1510 951 5false183656597M1610 843 C1509 846 1512 942 1510 951 5false183656598M1515 1473 C1514 1450 1512 1068 1510 1021 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656599M1615 1303 C1553 1303 1514 1139 1510 1021 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656600M1419 1107 C1486 1109 1508 1079 1510 1021 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656601M1430 1306 C1479 1305 1512 1083 1510 1021 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656602M1616 1110 C1564 1109 1511 1095 1510 1021 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656603M1155 201.5 L1155 251.5 L1205 201.5 z10true183656604M1515 1763 C1516 1805 1509 2102 1510 2133 5false183656605M1610 1982 C1558 1983 1511 2036 1510 2133 5false183656606M1430 1983 C1499 1985 1510 2052 1510 2133 5false183656607M1510 2638 C1510 2588 1511 2273 1510 2203 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656608M1590 2323 C1553 2320 1511 2267 1510 2203 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656609M1616 2514 C1586 2514 1511 2298 1510 2203 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656610M1389 2512 C1428 2513 1509 2327 1510 2203 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656611M1425 2331 C1464 2330 1509 2273 1510 2203 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3656612M1875 -21.5 L1875 28.5 L1925 -21.5 z10true183656864M1510 2928 C1511 2971 1510 3165 1510 3218 5false183656865M1601 3077 C1519 3078 1512 3133 1510 3218 5false183656866M1425 3078 C1472 3080 1510 3106 1510 3218 5false183656867M1515 3943 C1514 3834 1511 3400 1510 3288 5false18trueM 389.6135115383055 13.26155629629604 L 374.6666564941406 12 L 381.04754421532647 25.575134323078345false3656868M1606 3565 C1511 3561 1510 3357 1510 3288 5false18trueM 389.6135115383055 13.26155629629604 L 374.6666564941406 12 L 381.04754421532647 25.575134323078345false3656869M1424 3567 C1502 3569 1512 3417 1510 3288 5false18trueM 389.6135115383055 13.26155629629604 L 374.6666564941406 12 L 381.04754421532647 25.575134323078345false3656870M1605 3398 C1526 3395 1512 3350 1510 3288 5false18trueM 389.6135115383055 13.26155629629604 L 374.6666564941406 12 L 381.04754421532647 25.575134323078345false3656871M1425 3399 C1473 3401 1509 3369 1510 3288 5false18trueM 389.6135115383055 13.26155629629604 L 374.6666564941406 12 L 381.04754421532647 25.575134323078345false3656872M2640 -66.5 L2640 -16.5 L2690 -66.5 z10true183656892M1665 4083 C1816 4083 1840 4082 1940 4081 5false183656893M1845 4158 C1844 4112 1877 4081 1940 4081 5false183656894M1834 4013 C1833 4038 1878 4079 1940 4081 5false183656895M2365 4081 C2230 4081 2245 4080 2090 4081 5false18trueM 1478.9468550441647 13.26155629629604 L 1464 12 L 1470.380887721186 25.575134323078345false3656896M2195 4171 C2193 4115 2168 4081 2090 4081 5false18trueM 1478.9468550441647 13.26155629629604 L 1464 12 L 1470.380887721186 25.575134323078345false3656899M2515 3941 C2514 3717 2511 3441 2510 3330 5false183656900M2615 3493 C2565 3493 2511 3463 2510 3330 5false183656901M2439 3442 C2479 3443 2509 3416 2510 3330 5false183656902M2409 3552 C2467 3552 2510 3497 2510 3330 5false183656903M2510 2863 C2511 2991 2511 3115 2510 3260 5false18trueM 2173.6136030910397 13.26155629629604 L 2158.666748046875 12 L 2165.047635768061 25.575134323078345false3656904M2610 3101 C2565 3102 2511 3104 2510 3260 5false18trueM 1601.9657053123954 4385.333109739454 L 1610 4398 L 1616.9527014087807 4384.708651568771false3656905M2409 3100 C2479 3101 2510 3134 2510 3260 5false18trueM 2173.6136030910397 13.26155629629604 L 2158.666748046875 12 L 2165.047635768061 25.575134323078345false3656906M4105 -39.5 L4105 10.5 L4155 -39.5 z10true183656932M5195 -72 L5195 -22 L5245 -72 z10true183656933M2510 2573 C2511 2456 2506 2322 2510 2163 5false183656934M2395 2273 C2459 2273 2512 2221 2510 2163 5false183656935M2389 2472 C2475 2471 2511 2251 2510 2163 5false183656936M2611 2312 C2584 2311 2511 2320 2510 2163 5false183656937M2505 1738 C2505 1896 2511 1956 2510 2093 5false18trueM 3578.9468550441647 13.26155629629604 L 3564 12 L 3570.380887721186 25.575134323078345false3656938M2405 1933 C2442 1932 2508 1959 2510 2093 5false18trueM 3578.9468550441647 13.26155629629604 L 3564 12 L 3570.380887721186 25.575134323078345false3656939M2611 1942 C2572 1942 2510 1956 2510 2093 5false18trueM 3578.9468550441647 13.26155629629604 L 3564 12 L 3570.380887721186 25.575134323078345false3656943M2505 1448 C2502 1292 2511 1286 2510 1120 5false183656944M2600 1273 C2568 1271 2510 1246 2510 1120 5false183656945M2414 1282 C2446 1282 2511 1232 2510 1120 5false183656946M2414 1174 C2452 1174 2509 1165 2510 1120 5false183656947M2510 628 C2509 703 2510 945 2510 1050 5false18trueM 4748.280351137915 13.26155629629604 L 4733.33349609375 12 L 4739.714383814936 25.575134323078345false3656948M2405 928 C2468 927 2510 968 2510 1050 5false18trueM 4748.280351137915 13.26155629629604 L 4733.33349609375 12 L 4739.714383814936 25.575134323078345false3656949M2611 932 C2559 931 2509 977 2510 1050 5false18trueM 4748.280351137915 13.26155629629604 L 4733.33349609375 12 L 4739.714383814936 25.575134323078345false3656950M6390 -40 L6390 10 L6440 -40 z10true183656963M2660 483 C2799 483 2794 483 2935 483 5false183656964M2815 583 C2813 530 2845 482 2935 483 5false183656965M3360 484 C3245 484 3212 485 3085 483 5false18trueM 6126.946855044165 13.26155629629604 L 6112 12 L 6118.380887721186 25.575134323078345false3656966M3195 583 C3195 544 3182 484 3085 483 5false18trueM 6126.946855044165 13.26155629629604 L 6112 12 L 6118.380887721186 25.575134323078345false3656967M3229 401 C3229 455 3213 485 3085 483 5false18trueM 6126.946855044165 13.26155629629604 L 6112 12 L 6118.380887721186 25.575134323078345false3656968M3510 624 C3510 749 3510 745 3510 836 5false183656969M3610 744 C3551 743 3513 769 3510 836 5false183656970M3510 1184 C3510 1012 3510 1032 3510 906 5false18trueM 7009.613358950415 13.26155629629604 L 6994.66650390625 12 L 7001.047391627436 25.575134323078345false3656971M3620 1034 C3581 1033 3510 1027 3510 906 5false18trueM 7009.613358950415 13.26155629629604 L 6994.66650390625 12 L 7001.047391627436 25.575134323078345false3656972M3404 1033 C3454 1033 3512 1007 3510 906 5false18trueM 7009.613358950415 13.26155629629604 L 6994.66650390625 12 L 7001.047391627436 25.575134323078345false3656980M9760 203 L9760 253 L9810 203 z10true183656988M3510 1464 C3512 1604 3510 1712 3510 1823 5false183656989M3355 1553 C3451 1555 3511 1718 3510 1823 5false183656990M3611 1622 C3559 1622 3510 1638 3510 1823 5false183656991M3409 1712 C3454 1713 3511 1745 3510 1823 5false183656992M3510 2253 C3513 2036 3512 2145 3510 1893 5false18trueM 8089.613358950415 13.26155629629604 L 8074.66650390625 12 L 8081.047391627436 25.575134323078345false3656993M3405 2078 C3473 2079 3512 1983 3510 1893 5false18trueM 8089.613358950415 13.26155629629604 L 8074.66650390625 12 L 8081.047391627436 25.575134323078345false3656994M3606 2070 C3554 2068 3511 2012 3510 1893 5false18trueM 8089.613358950415 13.26155629629604 L 8074.66650390625 12 L 8081.047391627436 25.575134323078345false3657002M3510 2533 C3512 2672 3510 2799 3510 2907 5false183657003M3385 2652 C3444 2653 3511 2756 3510 2907 5false183657004M3429 2801 C3470 2801 3509 2832 3510 2907 5false183657005M3611 2759 C3558 2759 3510 2795 3510 2907 5false183657006M3510 3343 C3511 3229 3510 3127 3510 2977 5false18trueM 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2010.5751343230784false3657019M4210 3578 C4209 3523 4168 3481 4085 3482 5false18trueM 3298.9468550441647 1998.261556296296 L 3284 1997 L 3290.380887721186 2010.5751343230784false3657020M5240 2272.5 L5240 2322.5 L5290 2272.5 z10true183657030M4510 3343 C4508 3187 4509 3273 4510 3020 5false183657031M4615 3153 C4569 3152 4508 3124 4510 3020 5false183657032M4510 2531 C4509 2637 4511 2817 4510 2950 5false18trueM 4428.946855044165 1988.261556296296 L 4414 1987 L 4420.380887721186 2000.5751343230784false3657033M4610 2806 C4578 2808 4513 2835 4510 2950 5false18trueM 4428.946855044165 1988.261556296296 L 4414 1987 L 4420.380887721186 2000.5751343230784false3657034M4409 2810 C4449 2810 4510 2848 4510 2950 5false18trueM 4428.946855044165 1988.261556296296 L 4414 1987 L 4420.380887721186 2000.5751343230784false3657035M4510 2251 C4511 2064 4511 2015 4510 1898 5false183657036M4425 2086 C4459 2085 4510 2008 4510 1898 5false183657037M4510 1467 C4512 1604 4510 1779 4510 1828 5false18trueM 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