319PathwayEtoposide Metabolism PathwayEtoposide is an podophyllotoxin derative that is used in the treatment of certain cancers. It inhibits mitosis and induces cell death by acting as a topoisomerase II poison. Topoisomerase II is an enzyme in the nucleus of cells that unwinds DNA by making transient double-stranded breaks, relieving the torsion of supercoiled DNA. In the unwound form, DNA can serve as a template for DNA replication as well as transcription. In the normal state, this effect is transient and the breaks DNA are quickly religated by topoisomerase II itself. Etoposide, however, inhibits religation and stabilizes the DNA-topoisomerase II complex in the cleaved DNA form, ultimately leading to breaks in both DNA chains and cell death.
Etoposide is also converted into catechol and o-quinone derivatives in the liver and in lysosomes respectively. These metabolites are highly oxidative and can directly damage DNA, which may also contribute to the drug’s cytotoxic effects.Drug MetabolismPW000577CenterPathwayVisualizationContext64722002000#000099PathwayVisualization165319Etoposide PathwayEtoposide is an podophyllotoxin derative that is used in the treatment of certain cancers. It inhibits mitosis and induces cell death by acting as a topoisomerase II poison. Topoisomerase II is an enzyme in the nucleus of cells that unwinds DNA by making transient double-stranded breaks, relieving the torsion of supercoiled DNA. In the unwound form, DNA can serve as a template for DNA replication as well as transcription. In the normal state, this effect is transient and the breaks DNA are quickly religated by topoisomerase II itself. Etoposide, however, inhibits religation and stabilizes the DNA-topoisomerase II complex in the cleaved DNA form, ultimately leading to breaks in both DNA chains and cell death.
Etoposide is also converted into catechol and o-quinone derivatives in the liver and in lysosomes respectively. These metabolites are highly oxidative and can directly damage DNA, which may also contribute to the drug’s cytotoxic effects.Drug1414Etoposide inhibition of DNA topoisomeraseInhibitorySubPathway6379240Compound23638733ProteinComplex2313061076ProteinComplex23415Oxidative DNA Damage (Cell Death)SubPathway63940655Compound23789Etoposide ortho-quinone inhibition of DNA topoisomeraseInhibitorySubPathway130740655Compound231308733ProteinComplex2313091076ProteinComplex23790Etoposide catechol inhibition of DNA topoisomeraseInhibitorySubPathway131040656Compound231311733ProteinComplex2313121076ProteinComplex2314673006680Haim N, Roman J, Nemec J, Sinha BK: Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.319Pathway14683047665Holthuis JJ: Etoposide and teniposide. Bioanalysis, metabolism and clinical pharmacokinetics. Pharm Weekbl Sci. 1988 Jun 17;10(3):101-16.319Pathway14699381984Kizaki H, Onishi Y: Topoisomerase II inhibitor-induced apoptosis in thymocytes and lymphoma cells. Adv Enzyme Regul. 1997;37:403-23.319Pathway147017166655Montecucco A, Biamonti G: Cellular response to etoposide treatment. Cancer Lett. 2007 Jul 8;252(1):9-18. doi: 10.1016/j.canlet.2006.11.005. Epub 2006 Dec 12.319Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404Cardiomyocyte CL:00007467Epithelial CellCL:00000668Beta cellCL:00006391Homo sapiens9606EukaryoteHuman2Bacteria2ProkaryoteBacteria5Bos taurus9913EukaryoteCattle12Mus musculus10090EukaryoteMouse19Schizosaccharomyces pombe4896Eukaryote4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast10Drosophila melanogaster7227EukaryoteFruit fly17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia425Escherichia coli (strain K12)83333Prokaryote23Pseudomonas aeruginosa287Prokaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast15Plasmodium falciparum5833Eukaryote15NucleusGO:00056346LysosomeGO:00057645CytoplasmGO:000573711Extracellular SpaceGO:000561516Lysosomal LumenGO:00432027Endoplasmic Reticulum MembraneGO:00057891CytosolGO:00058294PeroxisomeGO:00057772MitochondrionGO:000573920Endoplasmic Reticulum LumenGO:000578813Endoplasmic ReticulumGO:00057838Smooth Endoplasmic Reticulum GO:000579010Cell MembraneGO:00058863Mitochondrial MatrixGO:000575912Mitochondrial Inner MembraneGO:000574314Mitochondrial Outer MembraneGO:000574125Golgi apparatusGO:000579427Peroxisome MembraneGO:000577826Golgi apparatus membraneGO:000013935ChloroplastGO:000950718Melanosome MembraneGO:003316221SynapseGO:004520231Periplasmic SpaceGO:000562036MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259732Inner MembraneGO:007025819sarcoplasmic reticulumGO:001652924Mitochondrial Intermembrane SpaceGO:00057581LiverBTO:00007597292Endothelium BTO:00003937Nervous SystemBTO:00014845cardiocyteBTO:00015398Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:00013071552611HeartBTO:0000562731018PancreasBTO:000098829111PW_BS000029231511PW_BS0000239611PW_BS0000098511PW_BS00000815111PW_BS0000152811611PW_BS00002816212PW_BS000016101711PW_BS0000102111PW_BS0000025411PW_BS0000053211PW_BS00000349711PW_BS0000493612011PW_BS000036181311PW_BS000018111811PW_BS000011261115PW_BS00002614101PW_BS0000144311PW_BS000004311511PW_BS000031951721PW_BS0000951231751PW_BS0001231251351PW_BS00012512915121PW_BS00012914117191PW_BS00014178811PW_BS00007811PW_BS000001151141PW_BS0001511601181PW_BS0001601613181PW_BS0001612137181PW_BS0000241985181PW_BS0000242111018PW_BS0000241644PW_BS00016429817101PW_BS00002430013101PW_BS000024171211PW_BS00001729341PW_BS0000242491341PW_BS0000241115121PW_BS00011113013121PW_BS0001303317121PW_BS00002833217121PW_BS0000281151012PW_BS0001153361121PW_BS0000283344121PW_BS0000281333121PW_BS0001331321121PW_BS0001321122121PW_BS00011213412121PW_BS000134405105PW_BS000115408451PW_BS000115407251PW_BS000115383751PW_BS000100429151PW_BS000115124151PW_BS000124122551PW_BS000122406351PW_BS0001153841251PW_BS0001003761017PW_BS00005344717171PW_BS00011513613171PW_BS0001363744171PW_BS0000531192171PW_BS0001193987171PW_BS0001134641171PW_BS0001151181171PW_BS0001181355171PW_BS0001351203171PW_BS00012012112171PW_BS0001214824101PW_BS0001154812101PW_BS0001152991101PW_BS0000242975101PW_BS0000244957101PW_BS0001154793101PW_BS00011548012101PW_BS000115502461PW_BS000115206261PW_BS000024388161PW_BS000112205561PW_BS0000243951361PW_BS000113390761PW_BS000112501361PW_BS0001153911261PW_BS000112221411PW_BS000022397113PW_BS000039215114PW_BS00002146114PW_BS000046432511PW_BS000043592711PW_BS000059711PW_BS000007918511PW_BS000091541315PW_BS000054562611PW_BS0000561041431PW_BS000104103331PW_BS0001031471241PW_BS0001471553241PW_BS00015516611PW_BS0001661783211PW_BS00017819914181PW_BS00002421425181PW_BS0000242164181PW_BS000024222341PW_BS00002421013181PW_BS0000242253541PW_BS0000242881441PW_BS000024226441PW_BS0000242905491PW_BS0000242851041PW_BS0000243081011PW_BS00002432914121PW_BS00002833527121PW_BS00002835625121PW_BS0000283683601PW_BS000028184121PW_BS000024372102PW_BS000028253541PW_BS0000245181PW_BS00005127151PW_BS0000272231241PW_BS0000243821451PW_BS0001004192551PW_BS0001154222751PW_BS00011539914171PW_BS00011345525171PW_BS00011537527171PW_BS00005348414101PW_BS00011549025101PW_BS0001154781010PW_BS00011549127101PW_BS0001153891461PW_BS0001125072561PW_BS000115209106PW_BS0000245082761PW_BS00011513121PW_BS000013204111PW_BS000020331811PW_BS0000332441011PW_BS00002460251PW_BS0000607028511PW_BS00007072513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS000093971521PW_BS000097100521PW_BS000100943PW_BS000094105113PW_BS0001051136121PW_BS000113110231PW_BS000110126651PW_BS00012612711651PW_BS0001271141112PW_BS00011410813PW_BS0001086131PW_BS000006140103PW_BS000140101531PW_BS00010114315191PW_BS0001431465191PW_BS000146107313PW_BS0001071572241PW_BS0001571632181PW_BS00016315924PW_BS0001591802211PW_BS00018015284PW_BS000152117131PW_BS000117188118PW_BS000024207661PW_BS0000242156181PW_BS00002421217181PW_BS000024224241PW_BS0000241901118PW_BS00002417018PW_BS00017016212181PW_BS0001622771218PW_BS0000242811251PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000242941141PW_BS000024315123PW_BS0000243183123PW_BS0000243221231PW_BS0000243331212PW_BS000028337116121PW_BS00002834141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115409115PW_BS0001154151851PW_BS0001154141551PW_BS0001154251355PW_BS00011543441051PW_BS000115436255PW_BS0001154436171PW_BS0001154461217PW_BS0001151371117PW_BS000137448116171PW_BS00011545118171PW_BS00011545015171PW_BS00011546013175PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154831110PW_BS00011548718101PW_BS000115208116PW_BS0000245041861PW_BS00011551541061PW_BS0001155131761PW_BS0001153211515PW_BS0000325811411PW_BS0000586618518PW_BS000066892PW_BS0000892171518PW_BS00002421815181PW_BS000024350114121PW_BS00002812815121PW_BS0001283511512PW_BS000028109323PW_BS00010943311451PW_BS0001154101551PW_BS000115435155PW_BS000115468114171PW_BS00011544415171PW_BS0001154701517PW_BS00011548515101PW_BS0001154991510PW_BS0001155161561PW_BS000115517156PW_BS000115471914PW_BS000047241529PW_BS00002425715291PW_BS00002430412PW_BS00002431323PW_BS0000249225711PW_BS000092422411PW_BS00004234524121PW_BS0000284182451PW_BS00011545424171PW_BS00011548924101PW_BS0001155062461PW_BS0001153551914PW_BS000035711113PW_BS0000717413PW_BS0000745311015PW_BS0000539911025PW_BS00009961415151PW_BS00050361517151PW_BS000503617116151PW_BS0005039240EtoposideHMDB0014911A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. [PubChem]33419-42-0C0157636462491133510DB00773[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1OC29H32O13InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1VJJPUSNTGOMMGY-MRVIYFEKSA-N(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one588.5566588.18429111-2.783(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one00(-)-etoposide;Etoposidum [inn-latin];Trans-etoposide;4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-beta-d-glucopyranoside);4-demethylepipodophyllotoxin beta-d-ethylideneglucoside;9-((4,6-o-ethylidine-beta-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5ah)-one;Eposin;Etopophos;Etoposido;Etoposidum;Lastet;Toposar;Vepesid;Vp-16;4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-b-d-glucopyranoside);4'-demethylepipodophyllotoxin 9-(4,6-o-(r)-ethylidene-β-d-glucopyranoside);4-demethylepipodophyllotoxin b-d-ethylideneglucoside;4-demethylepipodophyllotoxin β-d-ethylideneglucoside;9-((4,6-o-ethylidine-b-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5ah)-one;9-((4,6-o-ethylidine-β-d-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5ah)-onePW_C009240VP-162931292940233866940655Etoposide ortho-quinoneHMDB0061353Etoposide 3',4'-quinone belongs to the class of organic compounds known as furanonaphthodioxoles. These are aromatic heterocyclic compounds containing a 1,3-dioxole ring linearly fused to the a naphthofuran. Etoposide 3',4'-quinone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa).7632071331126076[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(=O)C(=O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1OC28H28O13InChI=1S/C28H28O13/c1-10-35-8-19-26(39-10)23(31)24(32)28(40-19)41-25-13-6-17-16(37-9-38-17)5-12(13)20(21-14(25)7-36-27(21)33)11-3-15(29)22(30)18(4-11)34-2/h3-6,10,14,19-21,23-26,28,31-32H,7-9H2,1-2H3/t10-,14+,19-,20-,21+,23-,24-,25-,26-,28+/m1/s1SBLYXIKLMHGUJZ-FMEAWWTOSA-N5-[(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl]-3-methoxycyclohexa-3,5-diene-1,2-dione572.5141572.152990982-2.4325-[(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl]-3-methoxycyclohexa-3,5-diene-1,2-dione00DBMET01265PW_C040655EtpOQn40709407423450984510154820281799HemeHMDB0003178Heme 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_C001799Heme24716308103248608276651244313544914133619631828062929389323811336726342114373444043314823285170955472123548512555171295830141624678628316597151704416070601617326213118351981189821112065164130092981302130042278177691529376931249773511117736413077367331773983327751711577629336778133347838013378602132789631127993213412043140512060340812095540712108538312165842912174612412191012212257040612269138412306537612313344712314413612322837412352111912365039812421646412429711812446313512514212012527712112574248212589648112619629912649929712651249512671847912682748012722450212735720612763238812807020512808339512808639012830950112843439140656Etoposide catecholHMDB0061352100007-54-3, also known as dhvp-16-213, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). 100007-54-3 is slightly soluble (in water) and a very weakly acidic compound (based on its pKa).127462113097[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(O)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1OC28H30O13InChI=1S/C28H30O13/c1-10-35-8-19-26(39-10)23(31)24(32)28(40-19)41-25-13-6-17-16(37-9-38-17)5-12(13)20(21-14(25)7-36-27(21)33)11-3-15(29)22(30)18(4-11)34-2/h3-6,10,14,19-21,23-26,28-32H,7-9H2,1-2H3/t10-,14+,19-,20-,21+,23-,24-,25-,26-,28+/m1/s1CYOJPLOJEPTJMM-FMEAWWTOSA-N(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(3,4-dihydroxy-5-methoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one574.53574.168641046-2.724(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(3,4-dihydroxy-5-methoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one00DBMET01264PW_C040656Etopcat4068294069945078450815481810423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951420WaterHMDB0002111Water 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_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153891034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389746Uridine diphosphate glucuronic acidHMDB0000935Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917).2616-64-0C001671747317200UDP-GLUCURONATE16522O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=OC15H22N2O18P2InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1HDYANYHVCAPMJV-LXQIFKJMSA-N(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid580.2853580.034284934-1.519udp-α-D-glucuronic acid0-3FDB022325Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate;Udp glucuronate;Udp glucuronic acid;Udp-d-glucuronate;Udp-d-glucuronic acid;Udp-glcua;Udp-glucuronate;Udp-glucuronic acid;Udp-alpha-d-glucuronate;Udp-alpha-delta-glucuronate;Udp-delta-glucuronate;Udp-delta-glucuronic acid;Udpga;Udpglucuronate;Uga;Uridine 5'-[3-(d-glucopyranosyloxyuronic acid) dihydrogen diphosphate];Uridine 5'-diphospho-a-d-glucuronate;Uridine 5'-diphospho-a-d-glucuronic acid;Uridine 5'-diphospho-alpha-delta-glucuronate;Uridine 5'-diphospho-alpha-delta-glucuronic acid;Uridine 5'-diphospho-glucuronic acid;Uridine 5'-diphosphoglucuronate;Uridine 5'-diphosphoglucuronic acid;Uridine diphosphate glucuronate;Uridine diphosphate glucuronic acid;Uridine diphosphate-glucuronate;Uridine diphospho-d-glucuronate;Uridine diphospho-d-glucuronic acid;Uridine diphospho-delta-glucuronate;Uridine diphospho-delta-glucuronic acid;Uridine diphosphoglucuronate;Uridine diphosphoglucuronic acid;Uridine pyrophosphoglucuronate;Uridine pyrophosphoglucuronic acid;Uridinediphosphoglucuronic acid;A-d-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);A-d-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Alpha-d-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);Alpha-delta-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Uridine-5'-diphosphate-glucuronic acid;Udp-a-d-glucuronate;Udp-a-d-glucuronic acid;Udp-α-d-glucuronate;Udp-α-d-glucuronic acid;Udpglucuronic acid;Uridine diphosphoric acid glucuronic acid;Uridine-5'-diphosphate-glucuronate;Uridine-5'-diphosphoric acid-glucuronic acidPW_C000746UDPGlcA11298221949230322351944791845161048443649449251769555251305832141705516077358331784031117861513212083012212204912412233838312341513512460311812488939812582129712620129912650649512727420512807839040592Etoposide glucuronideHMDB0060635Etoposide glucuronide belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Etoposide glucuronide is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Etoposide glucuronide 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, etoposide glucuronide is primarily located in the cytoplasm. In humans, etoposide glucuronide is involved in the etoposide metabolism pathway and the etoposide action pathway. Etoposide glucuronide is a metabolite of etoposide. Etoposide phosphate is an anticancer agent, which belongs to the drug type topoisomerase inhibitor. (Wikipedia)44881093685873COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2C35H40O19InChI=1S/C35H40O19/c1-11-46-9-20-30(50-11)25(38)27(40)34(51-20)52-28-14-7-17-16(48-10-49-17)6-13(14)21(22-15(28)8-47-33(22)43)12-4-18(44-2)29(19(5-12)45-3)53-35-26(39)23(36)24(37)31(54-35)32(41)42/h4-7,11,15,20-28,30-31,34-40H,8-10H2,1-3H3,(H,41,42)URCVASXWNJQAEH-UHFFFAOYSA-N6-{4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid764.6807764.216379098-2.5266-{4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid0-1DBMET00853PW_C040592EtpGlu38222938679451710201Uridine 5'-diphosphateHMDB0000295Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952).58-98-0C00015603117659UDP5809DB03435O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=OC9H14N2O12P2InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1XCCTYIAWTASOJW-XVFCMESISA-N[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid404.1612404.002196946-1.666UDP0-2FDB0075095'-udp;Udp;Uridine 5'-diphosphate;Uridine 5'-pyrophosphate;Uridine 5'-pyrophosphorate;Uridine 5'-pyrophosphoric acid;Uridine diphosphate;Uridine pyrophosphate;Uridine 5'-diphosphoric acid;Uridine diphosphoric acidPW_C000201UDP410815172154543219749235293115294463184518104846364946925178955527130583414170571607246213724821472872108433151119131641261522577304111773603317792433678255132782643561203151221212524291213651241213754191221013831223781251229701351238224641239241181239344551246523981249321361256432971260382991260484901262574951274903881275005071278203901065OxygenHMDB0001377Oxygen 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-Noxidanone31.998831.9898292440singlet oxygen00FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O2959110524516500185058549146252863836491067431688207541576347693383621375492016242531222803294260424747135467123548012554931265508127580910859731476129159700618870321637050160731921375332107560212839515111816216118641981188321511894211120572251206316412247286122792261232524912706291127162921300429813016300130263011303830213260223422761742657315769102937704429477214134773501117736313077377331773953327749711377512115775373347762633677723337777361127774712977756341778051147781213378070329781511327838134578805343791113601200474081203831221204264051205424071205534141205944091206014061208834151210451241211043831216054341216564291221173821225734181226893841227983741228224431230271351230603761231284471231391361231634481231761191231874501232191371232261201234594511236091181236693981241634691242144641246693991251454541252751211254254821257064781257314831257372971257404791258844811261002991262724841265224951267214891268254801269645021269862071271982091272142081272192051272225011273055041273452061275573881275745151278353891280813951280953901283125061284323911144NADHHMDB0001487NADH 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_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951102FormaldehydeHMDB0001426Formaldehyde 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_C001102Formol65310255532562445891854711235484125130082981302030077703332777101307808011278083133122126407122129406123132447123143136124678119124681120126283481126286479127846206127849501721NADHMDB0000902NAD (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]1OC21H28N7O14P2InChI=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)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-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_C000721NAD14041503353865110111421134431273514665422294927791728352931079480718481318481928490264960315167955238103533411153601125469123548212555901355610118569610057381085827141591214759421516024155607215760761616385164691786772117689016070121887097163717420571972067405198745922282412268359225908522411819216123222491300629813018300132562234240432242619315771041327712013377209134773703317765033677667334777023327770913077915113779833477840635680006368806901199382512411055238811275016611285394119929122119952406120171407120834419120984408121159425121242126121259429121817383122614384122742120123130447123141136123419455123549374123731460123812443123829464124370398125187121125319297125342479125530481125806299125825490125924482126515495126765480126885501127278507127383502128089390128360391128428395353CalciumHMDB0000464Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.14127-61-8C0007627129108CA%2b2266DB01373[Ca++]CaInChI=1S/Ca/q+2BHPQYMZQTOCNFJ-UHFFFAOYSA-Ncalcium(2+) ion40.07839.9625911550calcium(2+) ion22FDB003513Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ionPW_C000353Ca2+276163038553146012941159932199735104631163461164471478491491421552432116582138172796182937931597131607239422941866647821048222853401115780101717920572322117258160728119011774213118371981184221012198164122152851528815115350308693361773893317760011578154132782663567852634578724130789081148041374805892288182651120220122120465405121049124121300418121377419121850383121923125122370409122895135123099376123613118123870454123936455124403398124476136124924137125571297125711478125981489126009299126050490126533495127203209127434506127460388127502507128105390914Prostaglandin G/H synthase 1P23219May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
HMDBP00976PTGS19q32-q33.3M3181311.14.99.1248166162139249196418388296247781158588913Prostaglandin G/H synthase 2P35354Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
HMDBP00975PTGS21q25.2-q25.3M9010011.14.99.160921856491965183883962487865981511787Multidrug resistance protein 1P08183Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cellsHMDBP02101ABCB17q21.12M2942513.6.3.442976144924535218991750Canalicular multispecific organic anion transporter 2O15438May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytesHMDBP02040ABCC317q22BC137347132241484842284781DNA topoisomerase 2-alphaP11388Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaksHMDBP10697TOP2A17q21-q22AF07174015.99.1.32943231357016141360031281836DNA topoisomerase 2-betaQ02880Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Indirectly ivolved in vitamin D- coupled transcription regulation via its association with the WINAC complex, a chromatin-remodeling complex recruited by vitamin D receptor (VDR), which is required for the ligand-bound VDR- mediated transrepression of the CYP27B1 geneHMDBP02207TOP2B3p24AJ01172815.99.1.34511231357026141360041285738DnaJ homolog subfamily B member 11Q9UBS4DNAJB11AK07543013252236882938689389026443531445060448118451910518195422854913547611356876151359893325739HSP90B1 proteinQ96GW1HSP90B1 BC0091951325323689293869938912644363144516044821845201051829542286491354771135688615135990332574078 kDa glucose-regulated proteinP11021HSPA5AJ27172913254236902938709389226443731445260448318452110518395422874913547811356896151359913325741HYOU1 proteinQ6IN67HYOU1 BC07243613255236912938719389326443831445360448418452210518495422884913547911356906151359923325742Protein disulfide-isomerase A2Q13087PDIA2U1994815.3.4.13256236922938729389426443931445460448518452310518595422894913548011356916151359933325743Protein disulfide-isomerase A4P13667PDIA4BC00634415.3.4.13257236932938739389526444031445560448618452410518695422904913548111356926151359943325744Protein disulfide-isomerase A6Q15084PDIA6AK28942815.3.4.13258236942938749389626444131445660448718452510518795422914913548211356936151359953324776Peptidyl-prolyl cis-trans isomerase BP23284PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptidesHMDBP10692PPIB15q21-q22AY96231015.2.1.83259236952938759389726444231445760448818452610518895422924913548311356946151359963325745Stromal cell-derived factor 2-like protein 1Q9HCN8SDF2L1CR4565701326023696293876938982644433144586044891845271051899542293491354841135695615135997332465UDP-glucuronosyltransferase 1-1P22309UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
HMDBP00483UGT1A12q37M8412412.4.1.173261236972938779389926444431445960449018452810519095422944913548511356966151359983325746Endoplasmic reticulum resident protein 29P30040ERP29BC1014931326223698293878939002644453144606044911845291051919542295491354861135697615135999332956Cytochrome 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; 1.14.13.9729332932722329010336826404531457718517495135698615136000332136017491360183311442Cytochrome P450 3A5P20815Cytochromes 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.
HMDBP01554CYP3A57q21.1CH23695611.14.14.1293429327323369263436104044314590184339549135699615136001332276MyeloperoxidaseP05164Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
HMDBP00282MPO17q23.1X0487611.11.2.22939947831048242813570061713600233713605011363Prostaglandin G/H synthase 11PW_P0000637491423717991184Prostaglandin G/H synthase 21PW_P0001842029138217992738Multidrug resistance protein 11PW_P00073883317871799Canalicular multispecific organic anion transporter 21PW_P0007999041750733DNA topoisomerase 2-alpha1PW_P0007338274781232942342941231076DNA topoisomerase 2-beta1PW_P0010761236183614404232807UDP-glucuronosyltransferase 1-11PW_P000807912573819135739191457401915574119165742191757431918574419194776192057451921465192257461730Cytochrome P450 3A41PW_P000730824956132517991292910731Cytochrome P450 3A51PW_P0007318251442132617991293010732Myeloperoxidase1PW_P0007328262762327353232817992293592001falsePW_R002001Right721992401Compoundfalse7220406551Compoundfalse1846631.14.99.118471841.14.99.11957falsePW_R001957Right711992401Compoundfalse80347461Compoundtrue7120405921Compoundfalse80352011Compoundtrue18048075.3.4.11603falsePW_R001603Right611392401Compoundfalse865610651Compoundtrue865711441Compoundtrue6114406561Compoundfalse865814201Compoundtrue865911021Compoundtrue86607211Compoundtrue134073013417311.14.14.11604falsePW_R001604Right6115406561Compoundfalse86617211Compoundtrue6116406551Compoundfalse866211441Compoundtrue13427321.11.2.254PW_RCT000054Right319549240Compound131320541420Compound13132154414Compound131322549240Compound115323541104Compound131324541034Compound1315454134PW_T00013415692401Compound2923Right2127382013-10-07T14:42:25-06:002013-10-07T14:42:25-06:00142137992013-10-07T14:42:25-06:002013-10-07T14:42:25-06:0014246PW_T000246283406561Compound815Both247PW_T000247284406551Compound815Both5898924029157false68022510regular2001905905924023157false435147510regular200190819492403true61017510regular1001008195406553true109057510regular100110819617999false108554010regular10025819717999false108043510regular10025819840655233true102079010regular1001109343406568157true0010regular20019093444065615157false875147510regular2001909345406558157true0010regular20019093464065515157false1305147510regular2001909347423239false745194510regular100259348423239false930194510regular10025940214203149false48016010regular787894034143142false40518510regular5030940411043146false49338010regular4443940510343143false40539110regular5030940614203149false48064510regular787894074143142false41067010regular5030940811043146false49344510regular4443940910343143false40545110regular50309410746103false90516510regular10013094114059210157false150022510regular2001909412201103false127518010regular1001101059910651065false61344110regular78781060011441060false87046510regular5030106014065610157false67995510regular2001901060214201049false85979510regular7878106031102103false60478510regular100100106047211059false87475010regular5030106051799109false64757010regular10025106061799109false81257010regular10025106077212859false93494010regular5030106084065528157false150995510regular2001901060911442860false1399113010regular503010610353289false1134107010regular10025106111799289false1134100510regular1002541179142false10605508subunitregular1507041189132false10604458subunitregular15070516017871476false2552658subunitregular150705161175022876false2555408subunitregular1507051624781232false72018908subunitregular1507051631836232false90518908subunitregular1507051725738102true855858subunitregular1507051735739102true855858subunitregular1507051745740102true855858subunitregular1507051755741102true855858subunitregular1507051765742102true855858subunitregular1507051775743102true855858subunitregular1507051785744102true855858subunitregular1507051794776102true855858subunitregular1507051805745102true855858subunitregular15070518146510136false10452408proteinregular17515551825746102true10602308subunitregular150705727956102false6225808subunitregular1507057281442102false7875808subunitregular150705729276282false110910158subunitregular15070341063165409541171477819612335Cofactor3411184165409641181478819712336Cofactor424773816551335160424879916551345161424973316523513551621820934714744Cofactor4250107616523513651631821934814746Cofactor42588071651051445172514551735146517451475175514851765149517751505178515151795152518051535181515451824693730165105698572721701060516701Cofactor4694731165105699572821711060616702Cofactor4695732165285700572921721061016707Cofactor21731061116708Cofactor8964M435 1570 C226 1574 122 633 255 575 83false18trueM 552.5 847.0096189432334 L 560 860 L 567.5 847.0096189432334false8965M435 1570 C76 1561 39 296 255 300 83false18trueM 522.0818645747285 1312.6237639742023 L 535 1305 L 521.9385590132484 1297.6244485392883false12333M710 225 C740 225 226 28 250 45 5true1812334M1509 1050 C1386 1055 1318 513 1135 528 C1005 533 994 315 880 320 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false12335M325 255 L325 305 L375 255 z10true1812336M325 415 L325 465 L375 415 z10true1812337M1405 1665 C1407 1734 1162 1744 1165 1890 149false18trueM 1222.0096189432334 972.5 L 1235 965 L 1222.0096189432334 957.5false14735M405 575 C594 571 654 320 680 320 83false1814736M405 300 C432 301 651 320 680 320 83false1814739M11 12 C34 28 74 55 98 72 83true1814740M779 1145 C779 1168 975 1448 975 1475 83false18trueM 925.0644009829867 1208.611518094107 L 940 1210 L 933.7346610946918 1196.371150877582false14741M11 12 C34 28 74 55 98 72 83true1814742M1609 1145 C1609 1170 1404 1449 1405 1475 83false18trueM 1402.0062802889693 1197.307464982066 L 1410 1210 L 1416.995197908439 1196.730968150548false14743M11 12 C34 28 74 55 98 72 5true1814744M150 150 L150 200 L200 150 z10true1814745M635 1570 C658 1586 865 1504 889 1521 148true1814746M150 150 L150 200 L200 150 z10true1814747M978 1756 C977 1730 661 1570 635 1570 148false1814748M11 12 C34 28 74 55 98 72 5true1814749M975 1665 C976 1693 979 1865 980 1890 148false18falsetrueM 970.0119856191732 1605.599520575233 L 985 1605 L 999.9880143808268 1604.40047942476714750M978 1761 C978 1789 796 1869 795 1890 148false18falsetrueM 785.0169779341335 1604.2865227587683 L 800 1605 L 814.9830220658665 1605.713477241231714751M11 12 C34 28 74 55 98 72 148true1814752M11 12 C34 28 74 55 98 72 148true1814753M1305 1570 C1328 1586 978 1719 978 1757 148false1814838M880 320 C910 320 225 300 255 300 5true1814839M519 238 C520 265 431 299 405 300 5false1814840M430 215 C430 241 432 300 405 300 5false1814841M435 1570 C405 1570 435 300 405 300 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14842M515 380 C515 353 435 300 405 300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14843M430 391 C431 365 435 300 405 300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14844M880 320 C910 320 225 575 255 575 5true1814845M519 645 C518 617 433 576 405 575 5false1814846M435 670 C434 640 434 575 405 575 5false1814847M435 1570 C405 1570 435 575 405 575 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14848M515 488 C515 512 435 575 405 575 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14849M430 481 C431 505 435 575 405 575 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14850M880 320 C910 320 1020 320 1050 320 5false1814851M1005 230 C1035 230 1020 320 1050 320 5false1814852M1500 320 C1470 320 1250 320 1220 320 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false14853M1275 235 C1245 235 1250 320 1220 320 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345falsefalsefalse16694M780 415 C780 445 558 433 582 450 5true1816695M691 480 C718 481 779 562 780 615 5false1816696M870 480 C845 481 779 564 780 615 5false1816697M779 955 C779 925 779 462 780 415 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16698M859 834 C831 833 779 666 780 616 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16699M704 835 C728 835 779 683 779 615 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16700M874 765 C856 765 779 673 780 615 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16701M150 150 L150 200 L200 150 z10true1816702M150 150 L150 200 L200 150 z10true1816703M879 1050 C909 1050 1079 1050 1109 1050 5false1816704M959 970 C959 1000 1079 1050 1109 1050 5false1816705M1509 1050 C1479 1050 1289 1050 1259 1050 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16706M1424 1130 C1423 1100 1289 1050 1259 1050 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false16707M150 150 L150 200 L200 150 z10true1816708M150 150 L150 200 L200 150 z10true18242016520017949819412333Left7950819512334Right24711846341024721847341128421651957108874589814850Left8875941014851Left8876941114852Right8877941214853Right284718044258312716516031010087589816694Left100881059916695Left100891060016696Left100901060116697Right100911060216698Right100921060316699Right100931060416700Right3228134046933229134146943128165160428100941060116703Left100951060716704Left100961060816705Right100971060916706Right3230134246959054165530589814838Left531940214839Left532940314840Left533590514841Right534940414842Right535940514843Right944247659154165536589814844Left537940614845Left538940714846Left539590514847Right540940814848Right541940914849Right9542486622013416547158988964Left47259058965Right26442472122654248213385246165855934314739Left856934414740Right386247165857934514741Left858934614742Right744415165217false1090189016regular706819812337Left87941416514true0016regular822590514743Left519424914745Right520425014747Right88079016514true0016regular823934414748Left521424914749Right522425014750Right88178916514true0016regular824934614751Left523424914752Right524425014753Right13914735140147363357225101.01.00292001453366810559000.90.90252853207556617706600.80.815523280360358M330 179 C330 129 380 79 430 79 C821 79 1330 79 1721 79 C1771 79 1821 129 1821 179 C1821 475 1821 861 1821 1157 C1821 1207 1771 1257 1721 1257 C1330 1257 821 1257 430 1257 C380 1257 330 1207 330 1157 C330 861 330 475 330 179 1true61491.01178.0359M327 1479 C327 1429 377 1379 427 1379 C757 1379 1185 1379 1515 1379 C1565 1379 1615 1429 1615 1479 C1615 1649 1615 1869 1615 2039 C1615 2089 1565 2139 1515 2139 C1185 2139 757 2139 427 2139 C377 2139 327 2089 327 2039 C327 1869 327 1649 327 1479 1true61288.0760.0360M655 1839 C655 1789 705 1739 755 1739 C893 1739 1071 1739 1209 1739 C1259 1739 1309 1789 1309 1839 C1309 1871 1309 1912 1309 1944 C1309 1994 1259 2044 1209 2044 C1071 2044 893 2044 755 2044 C705 2044 655 1994 655 1944 C655 1912 655 1871 655 1839 93true6654.0305.0665M1133 162 C1135 320 1140 525 1128 563 C1092 633 744 614 606 614 91false6527.0452.033915Lysosome10401105201.01.01601565815Nucleus7101775201.01.01601565915Endoplasmic Reticulum1545610201.01.01601514182872312618771313394164612873481513551586144139966740#FFEEDE4813523