23PathwayCaffeine MetabolismCaffeine is obtained from diet including coffee and other beverages and is absorbed in the stomach and small intestine. In the liver, the cytochrome P450 oxidase enzyme system and specifically CYP1A2 metabolizes caffeine into paraxanthine to increase lipolysis and increase free fatty acids and glycerol levels in the blood, theobromine to dilate blood vessels and increase urine volume and theophylline which relaxes bronchi smooth muscles. In the lysosome, these metabolites undergo further metabolism into methyluric acids before being excreted in the urine. There is genetic variability in the metabolism of caffeine due to the polymorphism of CYP1A2. This variability can affect the pharmacokinetic and pharmacodynamic properties of caffeine and may affect an individual's consumption. MetabolicPW000015CenterPathwayVisualizationContext1527504100#000099PathwayVisualization2123Caffeine MetabolismCaffeine is obtained from diet including coffee and other beverages and is absorbed in the stomach and small intestine. In the liver, the cytochrome P450 oxidase enzyme system and specifically CYP1A2 metabolizes caffeine into paraxanthine to increase lipolysis and increase free fatty acids and glycerol levels in the blood, theobromine to dilate blood vessels and increase urine volume and theophylline which relaxes bronchi smooth muscles. In the lysosome, these metabolites undergo further metabolism into methyluric acids before being excreted in the urine. There is genetic variability in the metabolism of caffeine due to the polymorphism of CYP1A2. This variability can affect the pharmacokinetic and pharmacodynamic properties of caffeine and may affect an individual's consumption. Metabolic171Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.23Pathway72Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.23Pathway27977720164566Ribeiro JA, Sebastiao AM: Caffeine and adenosine. J Alzheimers Dis. 2010;20 Suppl 1:S3-15. doi: 10.3233/JAD-2010-1379.23Pathway27977819610047Gressner OA: Less Smad2 is good for you! A scientific update on coffee's liver benefits. Hepatology. 2009 Sep;50(3):970-8. doi: 10.1002/hep.23097.23Pathway27977929514871Nehlig A: Interindividual Differences in Caffeine Metabolism and Factors Driving Caffeine Consumption. Pharmacol Rev. 2018 Apr;70(2):384-411. doi: 10.1124/pr.117.014407. Epub 2018 Mar 7.23Pathway1CellCL:00000005HepatocyteCL:00001822Platelet CL:00002334CardiomyocyteCL:00007463NeuronCL:00005407Epithelial CellCL:00000669Pancreatic Beta CellCL:00001691Homo sapiens9606EukaryoteHuman5Bos taurus9913EukaryoteCattle10Drosophila melanogaster7227EukaryoteFruit fly12Mus musculus10090EukaryoteMouse17Rattus norvegicus10116EukaryoteRat4Arabidopsis thaliana3702EukaryoteThale cress2Bacteria2ProkaryoteBacteria3Escherichia coli562Prokaryote19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia449Bathymodiolus platifrons220390EukaryoteDeep sea mussel25Escherichia coli (strain K12)83333Prokaryote157Acinetobacter baumannii 107673Prokaryote15Plasmodium falciparum5833Eukaryote138human0046323Eukaryote7Endoplasmic Reticulum MembraneGO:00057891CytosolGO:000582916Lysosomal LumenGO:00432025CytoplasmGO:00057373Mitochondrial MatrixGO:00057592MitochondrionGO:00057394PeroxisomeGO:000577712Mitochondrial Inner MembraneGO:00057436LysosomeGO:000576413Endoplasmic ReticulumGO:000578335ChloroplastGO:000950710Cell MembraneGO:000588611Extracellular SpaceGO:000561518Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602025Golgi ApparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563431Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579027Peroxisome MembraneGO:000577839Mitochondrial membraneGO:00319661LiverBTO:00007597292Endothelium BTO:00003934Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273106KidneyBTO:000067171832Adrenal CortexBTO:000004518PancreasBTO:0000988101711PW_BS0000101231751PW_BS00012329817101PW_BS00002433217121PW_BS00002844717171PW_BS000115151141PW_BS0001512811611PW_BS00002829341PW_BS0000248511PW_BS000008122551PW_BS0001222975101PW_BS0000241115121PW_BS0001111355171PW_BS0001354311PW_BS0000043211PW_BS0000032111PW_BS0000025411PW_BS000005541315PW_BS00005449711PW_BS000049171211PW_BS00001729111PW_BS0000299611PW_BS000009181311PW_BS0000186131PW_BS000006311511PW_BS000031951721PW_BS000095103331PW_BS0001031122121PW_BS0001121251351PW_BS000125100521PW_BS00010010813PW_BS00010814117191PW_BS0001411471241PW_BS0001471553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS000178117131PW_BS0001171601181PW_BS000160188118PW_BS0000241632181PW_BS000163205561PW_BS000024206261PW_BS000024222341PW_BS000024226441PW_BS0000242253541PW_BS000024224241PW_BS0000241985181PW_BS0000242164181PW_BS0000242491341PW_BS00002430013101PW_BS0000242231241PW_BS0000243221231PW_BS000024315123PW_BS0000241321121PW_BS0001321333121PW_BS00013313412121PW_BS0001343317121PW_BS0000283361121PW_BS0000283344121PW_BS00002813013121PW_BS0001301136121PW_BS00011334713125PW_BS0000283683601PW_BS0000281192171PW_BS000119124151PW_BS000124388161PW_BS000112943PW_BS0000941181171PW_BS000118406351PW_BS000115407251PW_BS000115408451PW_BS0001154251355PW_BS000115126651PW_BS000126429151PW_BS000115383751PW_BS0001003841251PW_BS0001001203171PW_BS00012013613171PW_BS0001363744171PW_BS00005346013175PW_BS0001154436171PW_BS0001154641171PW_BS0001153987171PW_BS00011312112171PW_BS0001214793101PW_BS0001154812101PW_BS0001152991101PW_BS0000244824101PW_BS0001154957101PW_BS00011548012101PW_BS000115501361PW_BS000115502461PW_BS000115390761PW_BS0001123911261PW_BS0001123951361PW_BS000113185321PW_BS00002416212PW_BS00001614101PW_BS000014204111PW_BS00002015111PW_BS000015331811PW_BS0000332441011PW_BS000024221411PW_BS000022422411PW_BS00004213121PW_BS00001312711651PW_BS00012715924PW_BS0001592137181PW_BS00002421013181PW_BS00002421217181PW_BS0000242156181PW_BS0000242111018PW_BS0000241644PW_BS0001642863641PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000242941141PW_BS0000241151012PW_BS000115337116121PW_BS00002812915121PW_BS00012934141121PW_BS0000281141112PW_BS00011432914121PW_BS00002834524121PW_BS00002834318121PW_BS000028360410121PW_BS000028405105PW_BS0001154141551PW_BS000115409115PW_BS0001154151851PW_BS00011543441051PW_BS0001153821451PW_BS0001004182451PW_BS0001153761017PW_BS000053448116171PW_BS00011545015171PW_BS0001151371117PW_BS00013745118171PW_BS000115469410171PW_BS00011539914171PW_BS00011345424171PW_BS0001154781010PW_BS0001154831110PW_BS00011548414101PW_BS00011548924101PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS0000245041861PW_BS00011551541061PW_BS0001153891461PW_BS0001125062461PW_BS000115432511PW_BS0000431572241PW_BS00015735625121PW_BS00002816611PW_BS0001664192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS00011560251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097105113PW_BS000105110231PW_BS000110140103PW_BS000140101531PW_BS00010114315191PW_BS0001431465191PW_BS000146107313PW_BS0001071802211PW_BS00018015284PW_BS00015221425181PW_BS0000241901118PW_BS00002417018PW_BS00017016212181PW_BS000162261115PW_BS0000262771218PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000243081011PW_BS0000243183123PW_BS000024253541PW_BS0000243331212PW_BS0000283522512PW_BS00002835325127PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115436255PW_BS0001154461217PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS000549111811PW_BS00001178811PW_BS000078592711PW_BS0000595811411PW_BS0000581021231PW_BS0001021041431PW_BS00010419914181PW_BS0000241951318PW_BS000024350114121PW_BS00002833527121PW_BS0000282881441PW_BS00002443311451PW_BS0001154222751PW_BS000115468114171PW_BS00011537527171PW_BS00005349127101PW_BS0001155082761PW_BS0001151861221PW_BS0000248911421PW_BS0005525181PW_BS000051326812PW_BS00002841685PW_BS000115452817PW_BS000115488810PW_BS00011550586PW_BS00011515612241PW_BS00015617912211PW_BS0001793583912PW_BS00002836912601PW_BS00002884711PW_BS00054999611315PW_BS0005699731715PW_BS000569913111575PW_BS00055861517151PW_BS00050332517231PW_BS000024844131381PW_BS000549608321PW_BS00050169181019PW_BS000069392171PW_BS000171112125717PW_BS00058084241381PW_BS0005491222CaffeineHMDB0001847Caffeine is the most widely consumed psychostimulant drug in the world and is mostly consumed in the form of coffee. Whether caffeine and/or coffee consumption contributes to the development of cardiovascular disease (CVD), the single leading cause of death in the US, is unclear. The literature indicates a strong relationship between boiled, unfiltered coffee consumption and elevated cholesterol levels; however, there is a critical gap in the literature regarding the effects of coffee or caffeine consumption on fibrinogen or CRP, which is an independent predictor of CVD risk. Available studies are limited by small samples sizes, the inclusion of only men (or few women), and unrepresented age or ethnic groups. There is a critical need for controlled laboratory and epidemiological studies that include fibrinogen and CRP markers of CVD risk before conclusions can be drawn regarding the health effects of caffeine and/or coffee in a normal, healthy population of men and women (PMID: 16856769 ). The relationship between caffeine consumption and various illnesses such as cardiovascular disease and cancer remains equivocal. Prudence might dictate that pregnant women and chronically ill individuals exercise restraint in their use of caffeine, although research suggests relatively low or nonexistent levels of risk associated with moderate caffeine consumption (PMID: 7844249). There is extensive evidence that caffeine at dietary doses increases blood pressure (BP). However, concern that the drug may contribute to cardiovascular disease appears to have been dampened by (1) the belief that habitual use leads to the development of tolerance, and (2) confusion regarding relevant epidemiologic findings. When considered comprehensively, findings from experimental and epidemiologic studies converge to show that BP remains reactive to the pressor effects of caffeine in the diet. Overall, the impact of dietary caffeine on population BP levels is likely to be modest, probably in the region of 4/2 mm Hg. At these levels, however, population studies of BP indicate that caffeine use could account for premature deaths in the region of 14% for coronary heart disease and 20% for stroke (PMID: 14747639). Caffeine is a purine alkaloid that occurs naturally in coffee beans. At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form 5-acetylamino-6-amino-3-methyluracil. Caffeine concentrations in coffee beverages can be quite variable. A standard cup of coffee is often assumed to provide 100 mg of caffeine, but a recent analysis of 14 different specialty coffees purchased at coffee shops in the US found that the amount of caffeine in 8 oz (=240 ml) of brewed coffee ranged from 72 to 130 mg. Caffeine in espresso coffees ranged from 58 to 76 mg in a single shot (PMID: 16507475). Caffeine is a member of the methylxanthine family of drugs, and is the most widely consumed behaviourally active substance in the western world. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance, studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumour necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5), and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE) and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption (PMID: 16540173).58-08-2C074812519277322424DB00201CN1C=NC2=C1C(=O)N(C)C(=O)N2CC8H10N4O2InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3RYYVLZVUVIJVGH-UHFFFAOYSA-N1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione194.1906194.080375584-1.250caffeine00DBMET00535FDB0021001,3,7-trimethyl-2,6-dioxopurine;1,3,7-trimethyl-3,7-dihydro-1h-purine-2,6-dione;1,3,7-trimethylxanthine;1-methyl-theobromine;3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione;7-methyl theophylline;Anhydrous caffeine (jp15);Guaranine;Hycomine;Lanorinal;Methyltheobromide;Methylxanthine theophylline;Monohydrate caffeine;Propoxyphene;Thein;1,3,7-trimethylpurine-2,6-dione;1-methyltheobromine;3,7-dihydro-1,3,7-trimethyl-1h-purin-2,6-dion;7-methyltheophylline;Cafeina;Cafeine;Coffein;Koffein;Mateina;Methyltheobromine;Teina;TheinePW_C001222Cafeine64710546512313002298776993321231264471714TheobromineHMDB0002825Theobromine, or 3,7-Dimethylxanthine, is the principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9, as cited on Pubchem). Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine. Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus (Wikipedia).83-67-0C074805429289463-7-DIMETHYLXANTHINE5236DB01412CN1C=NC2=C1C(O)=NC(=O)N2CC7H8N4O2InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)YAPQBXQYLJRXSA-UHFFFAOYSA-N3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione180.164180.06472552-1.371theobromine00DBMET00220FDB000455Teobromin;2,6-dihydroxy-3,7-dimethyl-purine;3,7-dimethyl-xanthine;Diurobromine;Theobromine;3,7-dihydro-3,7-dimethyl-1h-purine-2,6-dione;3,7-dimethylpurine-2,6-dione;3,7-dimethylxanthine;TheobrominPW_C001714Thebrom6501054741231301129877075151777053321231354471257TheophyllineHMDB0001889Theophylline is a methylxanthine drug used in therapy for respiratory diseases such as Chronic obstructive pulmonary disease (COPD) or asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to caffeine. It is naturally found in black tea and green tea. A methyl xanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Theophylline inhibits the 3',5'-Cyclic nucleotide phosphodiesterase that degrades cyclic AMP (cAMP) thus potentiates the actions of agents that act through Adenylate cyclase and cAMP.58-55-9C07130215328177THF-GLU-N2068DB00277CN1C2=C(NC=N2)C(=O)N(C)C1=OC7H8N4O2InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)ZFXYFBGIUFBOJW-UHFFFAOYSA-N1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione180.164180.06472552-0.901theophylline00DBMET00221FDB0004531,3-dimethylxanthine;Accurbron;Acet-theocin;Aerolate;Aerolate iii;Aerolate sr;Aminophylline;Aquaphyllin;Armophylline;Asbron;Asmax;Austyn;Bronkodyl;Bronkodyl sr;Choledyl sa;Constant-t;Diphyllin;Doraphyllin;Duraphyl;Dyspne-inhal;Elixex;Elixicon;Elixomin;Elixophyllin;Elixophyllin sr;Elixophylline;Euphylline;Euphylong;Labid;Lanophyllin;Liquophylline;Liquorice;Maphylline;Medaphyllin;Nuelin;Optiphyllin;Parkophyllin;Pseudotheophylline;Quibron t/sr;Quibron-t;Quibron-t/sr;Respbid;Slo-bid;Slo-phyllin;Solosin;Somophyllin-crt;Somophyllin-df;Somophyllin-t;Spophyllin retard;Sustaire;Synophylate;Synophylate-l.a. cenules;T-phyl;Tefamin;Teofilina;Teofyllamin;Teolair;Theacitin;Theal tabl.;Theal tablets;Theo-dur;Theo-dur-sprinkle;Theobid;Theobid jr.;Theochron;Theocin;Theoclair-sr;Theoclear 80;Theoclear l.a.-130;Theoclear la;Theoclear-200;Theoclear-80;Theocontin;Theodel;Theofol;Theograd;Theolair;Theolair-sr;Theolix;Theolixir;Theona p;Theophyl;Theophyl-225;Theophyl-sr;Theophyline;Theophyllin;Theophylline anhydrous;Theophylline-sr;Theostat 80;Theovent;Uni-dur;Unifyl;Uniphyl;Uniphyllin;Xanthium;Xantivent;1,3-dimethyl-7h-purine-2,6-dionePW_C001257Asmax65510548112313017298777083321231404471234ParaxanthineHMDB00018601,7-dimethylxanthine (paraxanthine) is the preferential path of caffeine metabolism in humans. Paraxanthine is a dimethylxanthine compound structurally related to caffeine. Like caffeine, paraxanthine is a psychoactive central nervous system (CNS) stimulant. It possesses a potency roughly equal to that of caffeine and is likely involved in the mediation of the effects of caffeine itself.611-59-6C137474687258581-7-DIMETHYLXANTHINE4525CN1C=NC2=C1C(=O)N(C)C(=O)N2C7H8N4O2InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)QUNWUDVFRNGTCO-UHFFFAOYSA-N1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione180.164180.06472552-1.301paraxanthine00DBMET00223FDB0227141,7-dimethyl-xanthine;1,7-dimethylxanthine;3,7-dihydro-1,7-dimethyl-1h-purine-2,6-dione;P-xanthine;ParaxanthinePW_C001234Paraxnt65610546812313005298770731517770133212312944767451-MethylxanthineHMDB00107381-methylxanthine is the major metabolites of caffeine in the human. The oxidation of 1-methylxanthine to 1-methyluric acid occurred so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in brain. (PMID: 28863020.6136-37-4C16358802206844472464CN1C(=O)NC2=C(NC=N2)C1=OC6H6N4O2InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)MVOYJPOZRLFTCP-UHFFFAOYSA-N2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one166.1374166.049075456-1.1521-methylxanthine0-1DBMET00271C16358Methylxanthine;Purine analogPW_C0067451-Mxan6232866110549112313024298770711517771333212315044713357-MethylxanthineHMDB00019917-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites, including 7-methylxanthine. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. (PMID: 11712316, 15833286, 3506820, 15013152).552-62-5C1635368374489917-METHYLXANTHINE61660CN1C=NC2=C1C(=O)NC(=O)N2C6H6N4O2InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)PFWLFWPASULGAN-UHFFFAOYSA-N7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione166.1374166.049075456-1.3827-methylxanthine00DBMET00545FDB0019782,6-dihydroxy-7-methylpurine;3,7-dihydro-7-methyl-1h-purine-2,6-dione;7-methyl-3,7-dihydro-1h-purine-2,6-dione;7-methyl-7h-purine-2,6-diol;7-methylxanthin;Heteroxanthin;Heteroxanthine;MethylxanthinePW_C0013357MXantn66210549012313023298770772937771233212314944767485-Acetylamino-6-formylamino-3-methyluracilHMDB00111055-Acetylamino-6-formylamino-3-methyluracil, also known as afmu, belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5-Acetylamino-6-formylamino-3-methyluracil is considered to be a practically insoluble (in water) and relatively neutral molecule. 5-Acetylamino-6-formylamino-3-methyluracil has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 5-acetylamino-6-formylamino-3-methyluracil is primarily located in the cytoplasm. In humans, 5-acetylamino-6-formylamino-3-methyluracil is involved in the caffeine metabolism pathway. 5-Acetylamino-6-formylamino-3-methyluracil participates in Caffeine metabolism. 5-Acetylamino-6-formylamino-3-methyluracil is converted from paraxanthine via arylamine N-acetyltransferase [EC:2.3.1.5].85438-96-6C163651082143264397287CN1C(=O)NC(NC=O)=C(NC(C)=O)C1=OC8H10N4O4InChI=1S/C8H10N4O4/c1-4(14)10-5-6(9-3-13)11-8(16)12(2)7(5)15/h3H,1-2H3,(H,9,13)(H,10,14)(H,11,16)RDZNZFGKEVDNPK-UHFFFAOYSA-NN-(6-formamido-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide226.1894226.070204828-2.633AFMU00DBMET00612C163655-acetylamino-6-formylamino-3-methyluracil;AfmuPW_C0067485A6f3m66685463122130002977769711112312413521365-Acetylamino-6-amino-3-methyluracilHMDB00044005-Acetylamino-6-amino-3-methyluracil (AAMU) is one of caffeine major metabolites. Analysis of caffeine and its metabolites is of interest with respect to caffeine exposure, for kinetic and metabolism studies and for opportunistic in vivo estimation of drug metabolizing enzyme activity in humans and animals. Urinary caffeine metabolite ratios are used in humans to assess the activity of cytochrome P450 1A2 (CYP1A2), xanthine oxidase and N-acetyltransferase 2 (NAT2), which are involved in the activation or detoxification of various xenobiotic compounds, including carcinogens. Investigating the activity of these enzymes is of clinical relevance for assessing intra- and inter-individual differences in NAT2- and CYP1A2-mediated drug metabolism, and for evaluating the risk of developing specific exposure-related diseases. (PMID: 3506820, 15685651, 12534641).19893-78-8C163668829979659CN1C(=O)NC(N)=C(NC(C)=O)C1=OC7H10N4O3InChI=1S/C7H10N4O3/c1-3(12)9-4-5(8)10-7(14)11(2)6(4)13/h8H2,1-2H3,(H,9,12)(H,10,14)POQOTWQIYYNXAT-UHFFFAOYSA-NN-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide198.1793198.075290206-1.903N-(4-amino-1-methyl-2,6-dioxo-3H-pyrimidin-5-yl)acetamide00FDB0233715-ammu;AamuPW_C0021365A6A3M6688546412213001297776981111231251351144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951407591851065OxygenHMDB0001377Oxygen 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-Ndioxygen31.998831.9898292440singlet oxygen00FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=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](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H27N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium663.4251663.109121631-2.5281-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium0-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951407571851420WaterHMDB0002111Water 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-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851102FormaldehydeHMDB0001426Formaldehyde is a highly reactive aldehyde gas formed by oxidation or incomplete combustion of hydrocarbons. In solution, it has a wide range of uses: in the manufacture of resins and textiles, as a disinfectant, and as a laboratory fixative or preservative. Formaldehyde solution (formalin) is considered a hazardous compound, and its vapor toxic. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p717) -- Pubchem; The chemical compound formaldehyde (also known as methanal), is a gas with a pungent smell. It is the simplest aldehyde. Its chemical formula is H2CO. Formaldehyde was first synthesized by the Russian chemist Aleksandr Butlerov in 1859 but was conclusively identified by August Wilhelm van Hofmann in 1867. Although formaldehyde is a gas at room temperature, it is readily soluble in water, and it is most commonly sold as a 37% solution in water called by trade names such as formalin or formol. In water, formaldehyde polymerizes, and formalin actually contains very little formaldehyde in the form of H2CO monomer. Usually, these solutions contain a few percent methanol to limit the extent of polymerization. Formaldehyde exhibits most of the general chemical properties of the aldehydes, except that is generally more reactive than other aldehydes. Formaldehyde is a potent electrophile. It can participate in electrophilic aromatic substitution reactions with aromatic compounds and can undergo electrophilic addition reactions with alkenes. In the presence of basic catalysts, formaldehyde undergoes a Cannizaro reaction to produce formic acid and methanol. Because formaldehyde resins are used in many construction materials, including plywood, carpet, and spray-on insulating foams, and because these resins slowly give off formaldehyde over time, formaldehyde is one of the more common indoor air pollutants. At concentrations above 0.1 mg/kg in air, inhaled formaldehyde can irritate the eyes and mucous membranes, resulting in watery eyes, headache, a burning sensation in the throat, and difficulty breathing. -- Wikipedia.50-00-0C0006771216842FORMALDEHYDE692DB03843C=OCH2OInChI=1S/CH2O/c1-2/h1H2WSFSSNUMVMOOMR-UHFFFAOYSA-Nformaldehyde30.02630.0105646860.820formaldehyde00DBMET00531FDB009445Methaldehyde;Methylene glycol;Aldeide formica;Chlodithan;Chlodithane;Fannoform;Formaldehyde;Formalina;Formaline;Formalith;Formic aldehyde;Formol;Methanal;Methylene oxide;Oxomethylene;Paraform;Formaldehyd;Formalin;OxomethanePW_C001102Formol653102555325624458918547112354841251300829813020300777033327771013078080112780831331221264071221294061231324471231431361246781191246811201262834811262864791278462061278495011799HemeHMDB0003178Heme 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-L4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide616.487616.177297665-5.4824,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide0-2FDB016272(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_C001799Heme247163081032486082766512443135449141336196318280629293893238113367263421143734440433148232851709554721235485125551712958301416246786283165971517044160706016173262131183519811898211120651641300929813021300422781776915293769312497735111177364130773673317739833277517115776293367781333478380133786021327896311279932134120431405120603408120955407121085383121658429121746124121910122122570406122691384123065376123133447123144136123228374123521119123650398124216464124297118124463135125142120125277121125742482125896481126196299126499297126512495126718479126827480127224502127357206127632388128070205128083395128086390128309501128434391940Acetyl-CoAHMDB0001206The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.72-89-9C0002444449315351ACETYL-COA392413CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC23H38N7O17P3SInChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1ZSLZBFCDCINBPY-ZSJPKINUSA-N{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid809.571809.125773051-2.279acetyl-CoA0-4FDB022491Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme aPW_C000940Ac-CoA21343858842324162244652896173340114840145278103547612457331086025155607716163861647017869231607106163729119874602228245151827721012582226130122994261531577121133772911117756211277706132779941157835513478433334800073688063411980663376901241701199534061201454051203041221206324071224174081226263841227431201229591351231371181249863741252001211253434791255074781256332971265644821265724811267784801268865011270442091273942051276653881281375021281452061283743911407621851099Coenzyme AHMDB0001423Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).85-61-0C0001068161146900CO-A6557CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC21H36N7O16P3SInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1RGJOEKWQDUBAIZ-IBOSZNHHSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid767.534767.115208365-2.2210coenzyme A0-4FDB022614Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatePW_C001099CoA211438688453879228921724075924142245952813292862313342113351184618104629584842144865544879652321025247104528010354771245734108577710160231556075161638416468178693016069611626973199708318871081637293198734721074582228229151908122690902249124170921519513013299153182492548849426163157690729377119133772221347723032977292111775501327755533477563112776333367767212977996115780473327805635078413335785671307925933379974331800053688062011880627374806351198066537693828382938343839867428811055538911056139011584239911584739811995140612014740512023138412030512212063440712076211712140612312142143312152112512166642912168240812171441412240442212274112012290412112296013512396544712397946812407913612422046412426545012497437512534147912550947812557948012559248412563429712608448112654949112656048212674630012688450112704620912710939112730120512754020612766738812812150812813350212834039514075118614076318514076789117771-Methyluric acidHMDB00030991-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase, or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 superfamily, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID: 11712316, 15833286, 3506820, 15013152, 4039734, 9890610).708-79-2C16359697266844162926CN1C(=O)NC2=C(NC(=O)N2)C1=OC6H6N4O3InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)QFDRTQONISXGJA-UHFFFAOYSA-N1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione182.1368182.043990078-1.7531-methyluric acid00DBMET00560FDB0231071-MethyluratePW_C0017771MuricA62628483294833954941261302730177072151777141131231514431783Hydrogen peroxideHMDB0003125Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).7722-84-1C0002778416240HYDROGEN-PEROXIDE763OOH2O2InChI=1S/H2O2/c1-2/h1-2HMHAJPDPJQMAIIY-UHFFFAOYSA-Nperoxol34.014734.0054793082hydrogen peroxide00FDB014562Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;HoohPW_C001783H2O29891135188855114627287551512433169121749512534223818104749134752315495126550212355101275810108600514770381638396151118172161188621512461226127092911271929213028301130352981304030213405222426583157702222577047294770792937750011377540334775981157772033277725337778061147781011177819326780733297815213278598112120050408120102122120463405120595409120609416120954407121047124122120382122801374122814443122839135123097376123157447123165448123220137123234452123520119123611118124672399125428482125469297125709478125732483125748488125895481126103299126275484126967502126978207127006205127201209127215208127230505127356206127601388127838389964FADHMDB0001248FAD, 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-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid785.5497785.157134455-2.279flavine-adenine dinucleotide0-3FDB0225111h-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_C000964FAD9991145186819232164253176282882518840211881414894216122916224921335825362237232646023646883147411347581048816526810352851025335111549612655111275613118603015560541566082161611616263901647517864991796666107703916371752057321213746522274872239076224118182161188721511899211122962251232824912443151125192271259522612710291127202921302930113041302436233187708029377126133771521347750111377507112775181157754133477615132777263377805432978375345789303317922233679272358800123688003436980714119119958406119999384120051408120107407120432405120453122120490124121278429121298418121417382121489383122748120122776121122802374122823443123066376123087135123166448123849464123868454123976399124047398125348479125378480125429482125474481125697297125979489126107299126277484126891501126920391126968502126987207127011206127310209127432506127602388127840389140790185140799186405582Fe-2SHMDB0061344Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.S.S.[SH-].[SH-].[SH-].[SH-].[Fe++].[Fe++]Fe2H8S6InChI=1S/2Fe.6H2S/h;;6*1H2/q2*+2;;;;;;/p-4MZMMVZPHZTYDNI-UHFFFAOYSA-Jbis(lambda2-iron(2+) ion) disulfane tetrasulfanide312.11311.7648990bis(lambda2-iron(2+) ion) disulfane tetrasulfanide02PW_C0405582Fe2S374224012842571743893462654754314829948372850564549712655121277046160130303011304230277715113777273377837713478386132792071121178111331215864071217951241225673841226644061231524431231674481241441191243461181251401211252391201261892991267154801267964791276803881283063911283945011491MolybdopterinHMDB0002206Molybdenum cofactor is a cofactor required for the activity of enzymes such as sulfite oxidase, xanthine oxidoreductase, and aldehyde oxidase. It is a coordination complex formed between molybdopterin (which, despite the name, does not contain molybdenum) and an oxide of molybdenum. Molybdopterins, in turn, are synthesized from guanosine triphosphate. Molybdenum cofactor functions directly in ethylbenzene dehydrogenase, glyceraldehyde-3-phosphate ferredoxin oxidoreductase, and respiratory arsenate reductase. In animals and plants these enzymes use molybdenum bound at the active site in a tricyclic molybdenum cofactor. All molybdenum-using enzymes so far identified in nature use this cofactor The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia.73508-07-3C059242330423721437CPD0-18824883416O.O.[Mo++].[H]C1(COP(O)([O-])=O)OC2([H])NC3=C(NC2([H])C(S)=C1S)C([O-])=NC(=N)N3C10H16MoN5O8PS2InChI=1S/C10H14N5O6PS2.Mo.2H2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;2*1H2/q;+2;;/p-2VUKICSJFFDCESC-UHFFFAOYSA-Lmolybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate525.31526.923197-2.747molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate0-2FDB022906Moco;Molybdenum cofactor;Molybdenum enzyme molybdenum cofactor;Molybdoenzyme molybdenum-containing cofactor;Nitrate reductase molybdenum cofactor;Pterin molybdenum cofactorPW_C001491mlyBdpn1684817042391826395329438834627547533148309483828549812655131271203815113031301130433027771611377728337783851327920611212158540712179412412315344312316844812414311912434511812610829912767938867507-Methyluric acidHMDB00111077-Methyluric acid, also known as 7-methylate, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 7-Methyluric acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 7-Methyluric acid has been primarily detected in urine. In humans, 7-methyluric acid is involved in the caffeine metabolism pathway. 7-Methyluric acid is the minor urinary metabolites of caffeine. Caffeine is metabolized mainly in the liver undergoing demethylation and oxidation.612-37-3C163556916014974462375CN1C(=O)NC2=C1C(=O)NC(=O)N2C6H6N4O3InChI=1S/C6H6N4O3/c1-10-2-3(8-6(10)13)7-5(12)9-4(2)11/h1H3,(H3,7,8,9,11,12,13)YHNNPKUFPWLTOP-UHFFFAOYSA-N7-methyl-7H-purine-2,6,8-triol182.1368182.043990078-1.6937-methyluric acid00C16355PW_C0067507Ma6642848349550012613033301770782937771811312315544314281,3,7-Trimethyluric acidHMDB00021231,3,7-Trimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,3,7-Trimethyluracil is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152).5415-44-1C163617943769162271754CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2CC8H10N4O3InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)BYXCFUMGEBZDDI-UHFFFAOYSA-N1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione210.19210.075290206-0.8711,3,7-trimethyluric acid00DBMET00222FDB0228541,3, 7-trimethyluric acid;1,3,7-trimethyl-7,9-dihydro-1h-purine-2,6,8(3h)-trione;1,3,7-trimethylurate;2,6,8-trihydroxy-1,3,7-trimethylpurine;7,9-dihydro-1,3,7-trimethyl-1h-purine-2,6,8(3h)-trione;8-hydroxy-1,3,7-trimethyl-3,7-dihydro-1h-purine-2,6-dione;8-oxy-caffeine;Trimethyl uric acid;1,3,7-trimethyluric acid;1,3,7-trimethylate;1,3,7-trimethylic acidPW_C001428TriMurA382410482518550112313034298770832267771933212315644767461,7-Dimethyluric acidHMDB00111031,7-Dimethyluric acid, also known as 1,7-dimethylate, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 1,7-Dimethyluric acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1,7-Dimethyluric acid has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as feces, urine, and blood. Within the cell, 1,7-dimethyluric acid is primarily located in the cytoplasm. In humans, 1,7-dimethyluric acid is involved in the caffeine metabolism pathway. 1,7 dimethyluric acid is the major urinary caffeine metabolites that is produced in the human body. 1,7 dimethyluric acid is formed during metabolism of caffeine and the process is catalyzed primarily by CYP2A6. (PMID: 18715882).33868-03-0C16356916116844982720CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C7H8N4O3InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)9-7(14)11(2)5(3)12/h1-2H3,(H,8,13)(H,9,14)NOFNCLGCUJJPKU-UHFFFAOYSA-N2,8-dihydroxy-1,7-dimethyl-6,7-dihydro-1H-purin-6-one196.1634196.059640142-1.3621,7-dimethyluric acid0-1DBMET00611C1635617-dimethyluric acid;17-dimethylate;17-dimethylic acid;1,7-dimethylate;1,7-dimethylic acidPW_C0067461,7-DMA6652838171048269550512313036298770741517772133212316044713283,7-Dimethyluric acidHMDB00019823,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152).13087-49-5C16360831266853174994CN1C(=O)NC2=C1C(=O)NC(=O)N2CC7H8N4O3InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)11(2)7(14)9-5(3)12/h1-2H3,(H,8,13)(H,9,12,14)HMLZLHKHNBLLJD-UHFFFAOYSA-N3,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione196.1634196.059640142-1.3123,7-dimethyluric acid00DBMET00544FDB0227803,7-dimethyl-2,6,8-trihydroxypurine;3,7-dimethyl-7,9-dihydro-1h-purine-2,6,8(3h)-trione;37-dimethyluric acid;37-dimethylate;37-dimethylic acid;3,7-dimethylate;3,7-dimethylic acidPW_C0013283,7-DMA6632855091271303930277076151777243371231644481448Cytochrome P450 1A2P05177Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
HMDBP01560CYP1A215q24.1BC06742611.14.14.16541034221437882937942396226480818481418482795172951365673613966946139910298139913300140504847141115651426779961426789961427619731432Cytochrome P450 2E1P05181
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
HMDBP01544CYP2E110q24.3-qterJ0262511.14.13.-;1.14.13.n778110141749360029396426481118481718517195136042313962736139911298139917300141119651411248471419809131427009731429149964329Arylamine N-acetyltransferase 2A4Z6T9HMDBP09128NAT28p22DQ9041901667848052139912299956Cytochrome P450 3A4P08684Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
HMDBP01018CYP3A47q21.1M1890711.14.13.-; 1.14.13.157; 1.14.13.32; 1.14.13.67; 1.14.13.972933293272232901033682640453145771851749513569861513600033213601749136018331139914300139919298140218325140451847140803714084284414084511140956608141045691410803921411166514259199614268997314340111211450Cytochrome P450 2C8P10632Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
HMDBP01562CYP2C810q23.33AK29332811.14.14.11378493359293805104009264809184815181399153001399202981402133114104469141073847142762973973Cytochrome P450 2C9P11712Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
HMDBP01036CYP2C910q24AY34124811.14.13.-; 1.14.13.80; 1.14.13.48; 1.14.13.4933562934351038462404631481018481618138895491399163001399212981409588471410476914112065142592996142763973176Xanthine dehydrogenase/oxidaseP47989Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
HMDBP00181XDH2p23.1U3948711.17.1.4; 1.17.3.262928187253748240038483194964311399183011399233021404108421405121142077261455Cytochrome P450 2A6P11509Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
HMDBP01567CYP2A619q13.2AF32672111.14.13.-3267233602938191039632648289517595136067491399222981402113114050384714288099614288697321Arylamine N-acetyltransferase 2P11245Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
HMDBP00021NAT28p22DQ30557512.3.1.51360418190Cytochrome P450 1A21PW_P00019020814481861799163029226Cytochrome P450 2E11PW_P0002262441432110917991195Arylamine N-acetyltransferase 21PW_P000195213211730Cytochrome P450 3A41PW_P000730824956132517991292910383Cytochrome P450 2C81PW_P0003834051450117917991820Cytochrome P450 2C91PW_P000820944973135117991189Xanthine dehydrogenase/oxidase1PW_P000189207176285964139140558239214912821Cytochrome P450 2A61PW_P0008219451455135017991705truePW_R000705Right288467481Compoundfalse288521361Compoundfalse702falsePW_R000702Right286312221Compoundfalse286411441Compoundtrue286510651Compoundtrue286612341Compoundfalse28677211Compoundtrue286814201Compoundtrue286911021Compoundtrue2021901.14.14.1701falsePW_R000701Right285612221Compoundfalse285711441Compoundtrue285810651Compoundtrue285917141Compoundfalse28607211Compoundtrue286114201Compoundtrue286211021Compoundfalse2011901.14.14.11784226167falsePW_R000167Right74712341Compoundfalse86549401Compoundtrue74867481Compoundfalse865510991Compoundtrue2111952.3.1.5700falsePW_R000700Right284912221Compoundfalse285011441Compoundtrue285110651Compoundtrue285212571Compoundfalse28537211Compoundtrue285414201Compoundtrue285511021Compoundtrue2001901.14.14.1177973017803831.14.14.117818201782226704falsePW_R000704Right287712341Compoundfalse287811441Compoundtrue287910651Compoundtrue288013351Compoundfalse28817211Compoundtrue288214201Compoundtrue288311021Compoundtrue2061901.14.14.1703falsePW_R000703Right287012571Compoundfalse287111441Compoundtrue287210651Compoundtrue287367451Compoundfalse28747211Compoundtrue287514201Compoundtrue287611021Compoundtrue2031901.14.14.1580falsePW_R000580Right242967451Compoundfalse243014201Compoundtrue243110651Compoundtrue243217771Compoundfalse243317831Compoundtrue193189583falsePW_R000583Right244413351Compoundfalse244510651Compoundtrue244614201Compoundtrue244767501Compoundfalse244817831Compoundtrue2091891928falsePW_R001928Right705412221Compoundfalse855710651Compoundtrue855914201Compoundtrue705514281Compoundfalse856017831Compoundtrue17701901.14.14.1177173017723831.14.14.117738201774226581falsePW_R000581Right243412341Compoundfalse243510651Compoundtrue243614201Compoundtrue243767461Compoundfalse243817831Compoundtrue20518917871901.14.14.117888211.14.13.-582falsePW_R000582Right243917141Compoundfalse244014201Compoundtrue244110651Compoundtrue244213281Compoundfalse244317831Compoundtrue20418993212221081false260019510regular20019093517141081false288589010regular20019094012571081false233589010regular20019094212341081false175088510regular20019095067451081false2344175510regular20019095713351081false1944175510regular2001909826748881false1160124510regular2002009832136881false1160157510regular200200755511441060false182544010regular5030755610651065false170046510regular787875577211059false172570010regular5030755814201049false171075010regular7878755911021081false192067010regular20019075601799109false180558519regular10025764211441060false303547510regular5030764310651065false280045010regular787876447211059false286070510regular5030764514201049false283576010regular7878764611021081false305069010regular20019076471799109false284558510regular1002576481799109false251563010regular1002510536940281false116066010regular200190105371099285false1145109010regular50301057811441860false240244510regular50301057910651865false227344610regular7878105807211859false228574010regular50301058114201849false227079010regular7878105821102183false250574510regular100100105831799189false225754510regular10025105841799189false251754510regular10025105851799189false238759019regular10025105861799189false225763510regular10025105871799189false301258510regular100251064811441860false1912121510regular50301064910651865false2128119110regular7878106507211859false1934143510regular50301065114201849false1899149510regular78781065211021881false2089144010regular200190106531799189false1997131719regular100251065411441860false2292121010regular50301065510651865false2523118610regular7878106567211859false2324143510regular50301065714201849false2319149510regular78781065811021881false2514144010regular200190106591799189false2387131019regular10025106951420949false2281196010regular7878106961065965false2527196110regular7878106971777981false2341227510regular200190106981783956false2547217110regular78781069996499false2396208019regular10025107004055899false2391205519regular1002510701149199false2396214019regular10025107021065965false1907198110regular7878107031420949false2154196010regular7878107046750981false1946227010regular200190107051783956false2167217110regular78781070696499false1996208519regular10025107074055899false1996206519regular1002510708149199false1996214519regular100251072410651065false356345110regular78781072514201049false343543510regular78781072614281081false337289010regular2001901072717831056false330377110regular7878107281799109false353762010regular10025107291799109false355255010regular10025107301799109false342759019regular10025107311799109false330762010regular10025107321799109false330255010regular100251073310651065false1735119010regular78781073414201049false1485119010regular78781073567461081false1550175010regular2001901073617831056false1495145010regular7878107371799109false1535131010regular10025107381799109false1680131010regular100251073914202849false2837195510regular78781074010652865false3083195610regular78781074113282881false2887227510regular2001901074217832856false3093217110regular787810743964289false2942208519regular100251074440558289false29422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