31605PathwayEstrone MetabolismEstrone (also known as oestrone) is a weak endogenous estrogen, a steroid and minor female sex hormone. Estrone is synthesized from cholesterol and secreted from gonads. Endoplasmic reticulum (ER) is the place that estrone undergoes primary metabolism. Estrone sulfate and estrone glucuronide are the conjugated product of estrone; and CYP450 can hydroxylate estrone into catechol estrogens. The enzyme catechol O-methyltransferase catalyzes the conversion of 2-hydroxyestrone into 2-methoxyestrone which is used to synthesize 2-methoxyestrone 3-glucuronide via the membrane-associated massive multimer UDP-glucuronosyltransferase 1-1. Estrone can also be reversibly converted into estradiol by estradiol 17-beta-dehydrogenase 1. This same enzyme can reversibly convert 16a-hydroxyestrone (synthesized from estrone via cytochrome P450 3A5) into estriol. Estriol is alternatively synthesized from estradiol via cytochrome P450 3A5.MetabolicPW031778CenterPathwayVisualizationContext3205921242638#000099PathwayVisualization3153131605Estrone MetabolismEstrone (also known as oestrone) is a weak endogenous estrogen, a steroid and minor female sex hormone. Estrone is synthesized from cholesterol and secreted from gonads. Endoplasmic reticulum (ER) is the place that estrone undergoes primary metabolism. Estrone sulfate and estrone glucuronide are the conjugated product of estrone; and CYP450 can hydroxylate estrone into catechol estrogens. The enzyme catechol O-methyltransferase catalyzes the conversion of 2-hydroxyestrone into 2-methoxyestrone which is used to synthesize 2-methoxyestrone 3-glucuronide via the membrane-associated massive multimer UDP-glucuronosyltransferase 1-1. Estrone can also be reversibly converted into estradiol by estradiol 17-beta-dehydrogenase 1. This same enzyme can reversibly convert 16a-hydroxyestrone (synthesized from estrone via cytochrome P450 3A5) into estriol. Estriol is alternatively synthesized from estradiol via cytochrome P450 3A5.Metabolic18244111884392Pedersen LC, Petrotchenko E, Shevtsov S, Negishi M: Crystal structure of the human estrogen sulfotransferase-PAPS complex: evidence for catalytic role of Ser137 in the sulfuryl transfer reaction. J Biol Chem. 2002 May 17;277(20):17928-32. doi: 10.1074/jbc.M111651200. Epub 2002 Mar 7.31605Pathway1CellCL:00000005HepatocyteCL:00001822Platelet CL:00002334Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000666MyocyteCL:00001871Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia449Bathymodiolus platifrons220390EukaryoteDeep sea mussel15Plasmodium falciparum5833Eukaryote5CytoplasmGO:00057371CytosolGO:00058297Endoplasmic Reticulum MembraneGO:000578925Golgi apparatusGO:000579413Endoplasmic ReticulumGO:00057833Mitochondrial MatrixGO:000575911Extracellular SpaceGO:00056152MitochondrionGO:000573912Mitochondrial Inner MembraneGO:000574314Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562035ChloroplastGO:00095074PeroxisomeGO:000577710Cell MembraneGO:000588636MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:00702586LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579017NucleoplasmGO:000565439Mitochondrial membraneGO:003196627Peroxisome MembraneGO:000577826Golgi apparatus membraneGO:000013919sarcoplasmic reticulumGO:00165291LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274112Endothelium BTO:00003934Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273109MuscleBTO:0000887141185cardiocyteBTO:00015398511PW_BS0000082111PW_BS00000249711PW_BS0000491115121PW_BS0001113317121PW_BS0000281321121PW_BS000132122551PW_BS000122383751PW_BS000100124151PW_BS0001241355171PW_BS0001353987171PW_BS0001131181171PW_BS0001182975101PW_BS0000244957101PW_BS0001152991101PW_BS000024205561PW_BS000024390761PW_BS000112388161PW_BS000112432511PW_BS000043181311PW_BS000018311511PW_BS000031971521PW_BS00009714315191PW_BS00014321425181PW_BS000024151141PW_BS00015135625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS0001154311PW_BS00000415111PW_BS0000153211PW_BS000003261115PW_BS000026541315PW_BS000054171211PW_BS000017221411PW_BS000022422411PW_BS000042101711PW_BS0000107028511PW_BS000070103331PW_BS0001031122121PW_BS00011210813PW_BS000108107313PW_BS000107100521PW_BS000100105113PW_BS000105117131PW_BS0001171471241PW_BS0001471553241PW_BS0001551572241PW_BS0001571613181PW_BS00016115924PW_BS00015916611PW_BS0001661783211PW_BS00017815284PW_BS000152101531PW_BS000101188118PW_BS0000241873118PW_BS0000241632181PW_BS000163206261PW_BS000024219314PW_BS00002422014PW_BS000024222341PW_BS0000242137181PW_BS00002421013181PW_BS00002421217181PW_BS0000241601181PW_BS00016017018PW_BS0001702253541PW_BS000024226441PW_BS00002416212181PW_BS000162224241PW_BS0000241951318PW_BS0000242491341PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242231241PW_BS0000242941141PW_BS0000243081011PW_BS000024315123PW_BS0000243183123PW_BS0000243221231PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000241333121PW_BS00013313412121PW_BS0001341141112PW_BS00011432711125PW_BS00002834713125PW_BS00002834524121PW_BS00002813013121PW_BS0001303683601PW_BS000028310312PW_BS00002430412PW_BS0000241192171PW_BS000119943PW_BS0000943361121PW_BS000028109323PW_BS000109406351PW_BS000115407251PW_BS000115409115PW_BS0001154241155PW_BS0001154251355PW_BS0001154182451PW_BS0001153841251PW_BS0001001251351PW_BS0001251203171PW_BS0001201371117PW_BS00013745911175PW_BS00011546013175PW_BS00011545424171PW_BS00011512112171PW_BS00012113613171PW_BS0001364793101PW_BS0001154812101PW_BS0001154831110PW_BS00011548924101PW_BS00011548012101PW_BS00011530013101PW_BS000024501361PW_BS000115208116PW_BS0000245062461PW_BS0001153911261PW_BS0001123951361PW_BS0001139611PW_BS0000095411PW_BS00000516212PW_BS00001614101PW_BS0000142811611PW_BS000028204111PW_BS000020331811PW_BS0000332441011PW_BS00002429111PW_BS00002913121PW_BS0000131231751PW_BS000123126651PW_BS00012612711651PW_BS0001272164181PW_BS0000241985181PW_BS0000242156181PW_BS0000242111018PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS0000243016101PW_BS000024302116101PW_BS00002433217121PW_BS0000281136121PW_BS0001131151012PW_BS0001153344121PW_BS000028337116121PW_BS00002812915121PW_BS00012934141121PW_BS00002832914121PW_BS00002834318121PW_BS000028360410121PW_BS000028408451PW_BS000115405105PW_BS0001154141551PW_BS0001154151851PW_BS00011543441051PW_BS000115429151PW_BS0001153821451PW_BS0001003744171PW_BS0000534436171PW_BS0001153761017PW_BS00005344717171PW_BS000115448116171PW_BS00011545015171PW_BS00011545118171PW_BS000115469410171PW_BS0001154641171PW_BS00011539914171PW_BS0001134824101PW_BS0001154781010PW_BS00011548414101PW_BS000115502461PW_BS000115207661PW_BS000024209106PW_BS0000245041861PW_BS00011551541061PW_BS0001153891461PW_BS0001126131PW_BS000006951721PW_BS00009514117191PW_BS00014111PW_BS00000160251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007110231PW_BS000110140103PW_BS0001401465191PW_BS0001461802211PW_BS0001801901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS000024253541PW_BS0000243331212PW_BS0000283522512PW_BS00002835325127PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115436255PW_BS0001154461217PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS0001155131761PW_BS000115111811PW_BS00001178811PW_BS000078301711PW_BS000030509516PW_BS0000503093911PW_BS00002433817121PW_BS0000283511512PW_BS00002834695126PW_BS00002836139121PW_BS0000283863951PW_BS0001003973961PW_BS00011340139171PW_BS0001134131751PW_BS000115435155PW_BS00011544917171PW_BS0001154701517PW_BS0001154991510PW_BS000115517156PW_BS000115397113PW_BS000039215114PW_BS000021592711PW_BS000059231511PW_BS000023918511PW_BS000091562611PW_BS0000561041431PW_BS00010419914181PW_BS0000242881441PW_BS00002433527121PW_BS000028184121PW_BS000024372102PW_BS0000285181PW_BS0000514222751PW_BS00011537527171PW_BS00005349127101PW_BS0001155082761PW_BS0001159225711PW_BS0000923551914PW_BS00003539451PW_BS00017661517151PW_BS00050394EstroneHMDB0000145Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961, 17513923, 17470679, 17464097).53-16-7C00468587017263ESTRONE5660DB00655[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3C18H22O2InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1DNXHEGUUPJUMQT-CBZIJGRNSA-N(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one270.3661270.161979948-4.841(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one00DBMET00490FDB012798(+)-estrone;1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-17-keto-estra-1,3,5-triene;3-hydroxyestra-1,3,5(10)-trien-17-one;3-hydroxyestra-1,3,5(10)-triene-17-one;3-hydroxyoestra-1,3,5(10)-trien-17-one;D1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-1,3,5(10)-estratrien-17-one;Follicular hormone;Folliculin;OestronePW_C000094Estrone3408140124229849773451117992733179982132120962122122685383122698124123527135125271398125285118125902297126820495126836299127363205128425390128443388886Phosphoadenosine phosphosulfateHMDB00011343'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.482-67-7C000531021417980PAPS9799NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1OC10H15N5O13P2SInChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1GACDQMDRPRGCTN-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid507.264506.986229305-2.0063'-phosphoadenylyl sulfate0-4FDB0224453'-phospho-5'-adenylyl sulfate;3'-phosphoadenosine 5'-phosphosulfate;3'-phosphoadenosine-5'-phosphosulfate;3'-phosphoadenylyl sulfate;3'-phosphoadenylyl-sulfate;5-phosphoadenosine 3-phosphosulfate;Paps;Phosphoadenosine phosphosulfate;3'-phospho-5'-adenylyl sulphate;3'-phosphoadenosine 5'-phosphosulphate;3'-phosphoadenosine-5'-phosphosulphate;3'-phosphoadenylyl sulphate;3'-phosphoadenylyl-sulphate;5-phosphoadenosine 3-phosphosulphate;Phosphoadenosine phosphosulphate;3'-phosphoadenosine 5'-phosphosulfuric acid;3'-phosphoadenosine 5'-phosphosulphuric acidPW_C000886Paps124982205434585184893315198975843143725121484361514337627734611178887356799831321209601221221064191226991241235251351246574551252861181259002971262614901268372991273612051278255071284443881101Estrone sulfateHMDB0001425Estrone sulfate is a sulfated estrone derivative. Estrone sulfate acts as a long-lived reservoir that can be converted as needed to the more active estradiol (from estrone via 17 beta-hydroxysteroid dehydrogenase). Estrone Sulfate (E1S) is the most abundant circulating estrogen in non-pregnant women as well as normal men. Estrone is primarily synthesized from estrone sulfate. Estrone is an estrogenic hormone secreted by the ovaries and adipose tissues. Estrone is one of the three estrogens found in humans. The other two are estriol and estradiol. Estrone is the least prevalent of the three. Estradiol plays a critical role on reproductive and sexual functioning in women and it also affects other organs including the bones. Estriol is an estrogen that is prevalent primarily during pregnancy.481-97-0C02538300102817474ESTRONE-SULFATE2272513DB04574C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=OC18H22O5SInChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1JKKFKPJIXZFSSB-CBZIJGRNSA-N[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid350.429350.118794504-4.771Ogen0-1DBMET00530FDB021804Conestoral;Estrogenic substances;Estrone;Estrone hydrogen sulfate;Estrone 3-sulfate;Estrone sulfate;Estrone sulfate sodium;Estrone-3-sulfate;Premarin;Sodium estrone 3-monosulfate;Sodium estrone 3-sulfate;Estrone hydrogen sulphate;Estrone 3-sulphate;Estrone sulphate;Estrone sulphate sodium;Estrone-3-sulphate;Sodium estrone 3-monosulphate;Sodium estrone 3-sulphate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphate;Estrone hydrogen sulfate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfuric acid;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphuric acid;Estrone 3-sulfuric acid;Estrone 3-sulphuric acid;Estrone hydrogen sulfuric acid;Estrone hydrogen sulphate;Estrone hydrogen sulphuric acid;Estrone sulfuric acid;Estrone sulphuric acidPW_C001101Estrone341814022773471117998413212096412212270012412352913512528711812590429712683829912736520512844538843Adenosine 3',5'-diphosphateHMDB0000061Adenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy.1053-73-2C00054159296179853-5-ADP140102NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1WHTCPDAXWFLDIH-KQYNXXCUSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid427.2011427.029414749-2.116adenosine 3',5'-bisphosphate0-4FDB0218873'-phosphoryl-amp;3,5-adp;3,5-diphosphoadenosine;3-phosphoadenosine 5-phosphate;5-(dihydrogen phosphate) 3-adenylate;5-(dihydrogen phosphate)3'-adenylic acid;Adenosine 3',5'-bisphosphate;Adenosine 3,5-bis;Adenosine 3,5-bisphosphate;3'-phosphoadenylate;Pap;Phosphoadenosine phosphate;3'-phosphoadenylic acid;Adenosine 3',5'-bismonophosphoric acid;Adenosine 3',5'-bisphosphoric acid;Phosphoadenosine phosphoric acidPW_C000043A3'5'PP1251822074345871848953152009758451437253214843715143377277348111788893567998513212096312212210841912270112412352813512465945512528811812590329712626349012683929912736420512782750712844638840034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951065OxygenHMDB0001377Oxygen 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_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293952442-HydroxyestroneHMDB0000343Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.362-06-1C052984406231156389514[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3C18H22O3InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1SWINWPBPEKHUOD-JPVZDGGYSA-N(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one286.3655286.15689457-4.092(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one00FDB0219662,3-dihydroxyestra-1,3,5(10)-trien-17-one;2-hydroxyestrone;2-ohe1;CatecholestronePW_C0002442-Ohe1433794979987331122703383125290398126841495128447390721NADHMDB0000902NAD (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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131799HemeHMDB0003178Heme 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_C001799Heme247163081032486082766512443135449141336196318280629293893238113367263421143734440433148232851709554721235485125551712958301416246786283165971517044160706016173262131183519811898211120651641300929813021300422781776915293769312497735111177364130773673317739833277517115776293367781333478380133786021327896311279932134120431405120603408120955407121085383121658429121746124121910122122570406122691384123065376123133447123144136123228374123521119123650398124216464124297118124463135125142120125277121125742482125896481126196299126499297126512495126718479126827480127224502127357206127632388128070205128083395128086390128309501128434391921S-AdenosylmethionineHMDB0001185S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.485-80-3C000192476216515414S-ADENOSYLMETHIONINE31983DB00118C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NC15H23N6O5SInChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1MEFKEPWMEQBLKI-AIRLBKTGSA-O[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium399.445399.145063566-2.565SAMe11FDB022473(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;SamePW_C000921SAMe51986333070420122031880272066246811050235056041357136163754021075442137632160826615192351951187419812031222123582251529324915345181536330976897293768991647698422477488111777313387777234178099132783033517833534679155112799613618086122948303829483338611328638911328839711554339911554640112039312212053741312093940712105212412228243512317144912350511912361611812483647012585929712587948112630429912644749912732120512734020612759538812801751752-MethoxyestroneHMDB00000102-Methoxyestrone is a steroid derivative that is a byproduct of estrone and 2-hydroxyestrone metabolism. It is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone is 10.81 (PMID: 516114). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17).362-08-3C052994406241189389515[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3C19H24O3InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1WHEUWNKSCXYKBU-QPWUGHHJSA-N(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one300.3921300.172544634-4.601(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one00FDB0218682-(8s,9s,13s,14s)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one;2-hydroxyestrone 2-methyl ether;2-methoxy-17-oxoestra-1,3,5(10)-trien-3-ol;2-methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one;3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one;3-hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one;Methoxy-estrone;2-methoxyestronePW_C0000052-MeOxE43381279989132122704124125292118126842299128449388749S-AdenosylhomocysteineHMDB0000939S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).979-92-0C000212524622216680ADENOSYL-HOMO-CYS388301N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=OC14H20N6O5SInChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1ZJUKTBDSGOFHSH-WFMPWKQPSA-N(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid384.411384.12158847-1.975S-adenosyl-L-homocysteine00DBMET00514FDB022327(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteinePW_C000749SAH5208575186353070520122131882272067246831050255056071367137163754221075462137634160826815192371951187519812359225152942491536430977489111776111307773333877773341780981327830535178337346791561127996236180863229483138294834386113287389113289397115544399115547401120394122120486125120539413120940407121053124122284435123037135123173449123506119123617118124838470125880481126303299126449499127341206127596388128019517423MagnesiumHMDB0000547Magnesium 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+86822742681647627272681158191888322936399833992211167461483491529431764142124102411592942233126293373745403147749148695449745652531045329111535611253761035906147593415160381556094161625016664841786594164688116069791997170205719420672272137233211725021473102167313198747322211763132118432101231222512324249125132881258122612729290152752851533730877137133772363297793733678393334784173357848911578522331785363567857413080020368800451848004837280623118806541358086515809652538184151938323839490027108596223110559390115687398119974406120070122120247382120702407120981408121181124121265429121319419121924125122086405122408422122759120122921399123307119123546374123835464123889455124477136124637376124978375125447297125598484125669479125777481125921482125947299125973495126000490126243478126553491126753300127125389127164501127380502127407388127451507127804209128125508128347395746Uridine 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_C000746UDPGlcA11298221949230322351944791845161048443649449251769555251305832141705516077358331784031117861513212083012212204912412233838312341513512460311812488939812582129712620129912650649512727420512807839021422-Methoxyestrone 3-glucuronideHMDB00044822-Methoxyestrone 3-glucuronide is a natural human metabolite of 2-Methoxyestrone generated in the liver by UDP glucuonyltransferase. A glucuronide conjugate of 2-methodxyestrone formed by UDP-glucuronylstransferase (UTP). 2-methoxyestrone is a metabolite of 2-hydroxyestrone (a nonuterotrophic metabolite of estradiol). Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.25577-70-2C1113222833612ESTRONE-SULFATE17216256[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC(OC)=C(O[C@@H]4O[C@H](O)[C@@H](O)[C@H](O)[C@H]4O)C=C3CC[C@@]21[H]C24H32O8InChI=1S/C24H32O8/c1-24-8-7-12-13(15(24)5-6-18(24)25)4-3-11-9-17(16(30-2)10-14(11)12)31-23-21(28)19(26)20(27)22(29)32-23/h9-10,12-13,15,19-23,26-29H,3-8H2,1-2H3/t12-,13+,15-,19-,20-,21+,22-,23+,24-/m0/s1CLTGLDLWQUZPJU-OOJOVCNMSA-N(1S,10R,11S,15S)-4-methoxy-15-methyl-5-{[(2R,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-14-one448.5061448.209718-3.0542-methoxyestrone 3-glucuronide00DBMET00568FDB0233752-methoxyestrone-3-glucuronide;2-methoxyestrone-3-glucuronosidePW_C0021422M3g433864979990331122705383125293398126843495128450390201Uridine 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_C000201UDP410815172154543219749235293115294463184518104846364946925178955527130583414170571607246213724821472872108433151119131641261522577304111773603317792433678255132782643561203151221212524291213651241213754191221013831223781251229701351238224641239241181239344551246523981249321361256432971260382991260484901262574951274903881275005071278203902143Estrone glucuronideHMDB0004483Estrone-glucuronide is the dominant metabolite of estradiol. Estrone glucuronide is formed by a UDP glucuronyltransferase (EC 2.4.1.17, UTP) reaction creating a much more water-soluble form of the hormone; glucuronides are the most abundant estrogen conjugates. Measurement of estrone-glucuronide is used as one reference method for determining ovulation (immunotubes are available for measuring urinary estrone glucuronide in conjunction with LH, one of the most advanced of ovulation prediction products). (PMID: 14742773, 1755456).2479-90-5C1113311525528919ESTRONE-SULFATE103124[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]C24H30O8InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1FJAZVHYPASAQKM-JBAURARKSA-N(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid446.4902446.194067936-3.174estrone-3-glucuronide0-1DBMET00569FDB021803Estrone 3-glucuronide;Estrone beta-d-glucuronide;Estrone beta-delta-glucuronide;Estrone-3-glucosiduronic acidPW_C002143EstrGlu433914979991331122706383125294398126844495128451390146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1ACFIXJIJDZMPPO-NCHANQSKSA-N{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid745.4209745.091102105-2.149[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid0-4FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139098EstradiolHMDB0000151Estradiol is the most potent form of mammalian estrogenic steroids. Estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600, 17678531, 17644764).50-28-2C00951575716469CPD-3525554DB00783[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3C18H24O2InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1VOXZDWNPVJITMN-ZBRFXRBCSA-N(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol272.382272.177630012-4.112(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol00DBMET00491FDB000362(+)-3,17b-estradiol;(17b)-estra-1,3,5(10)-triene-3,17-diol;13b-methyl-1,3,5(10)-gonatriene-3,17b-ol;17b-estradiol;17b-oestradiol;3,17-epidihydroxyestratriene;3,17b-dihydroxyestra-1,3,5(10)-triene;3,17b-estradiol;Aerodiol;Agofollin;Altrad;Amnestrogen;Aquadiol;Bardiol;Climaderm;Climara;Compudose;Corpagen;D-estradiol;D-oestradiol;Dermestril;Dihydro-theelin;Dihydrofollicular hormone;Dihydrofolliculin;Dihydromenformon;Dihydrotheelin;Dihydroxyestrin;Dimenformon;Diogyn;Diogynets;Divigel;Encore;Epiestriol 50;Estra-1,3,5(10)-triene-3,17b-diol;Estrace;Estraderm tts;Estradiol;Estradiol-17-beta;Estradot;Estraldine;Estring vaginal ring;Estroclim;Estroclim 50;Estrogel;Estrogel hbf;Estrovite;Evorel;Femestral;Femogen;Follicyclin;Gelestra;Ginosedol;Gynergon;Gynoestryl;Lamdiol;Macrodiol;Menorest;Nordicol;Oesclim;Oestergon;Oestra-1,3,5(10)-triene-3,17b-diol;Oestradiol;Oestrogel;Oestroglandol;Ovahormon;Ovasterol;Ovastevol;Ovocyclin;Ovocylin;Perlatanol;Primofol;Profoliol;Profoliol b;Progynon;Progynon dh;Sandrena 1;Syndiol;Systen;Vivelle;Zumenon;B-estradiol;Beta-estradiol;Delta-estradiol;Delta-oestradiol;(17beta)-estra-1,3,5(10)-triene-3,17-diol;17beta oestradiol;17beta-estra-1,3,5(10)-triene-3,17-diol;17beta-oestradiol;Cis-estradiol;Estradiol-17beta;(17β)-estra-1,3,5(10)-triene-3,17-diol;17b oestradiol;17β oestradiol;17b-estra-1,3,5(10)-triene-3,17-diol;17β-estra-1,3,5(10)-triene-3,17-diol;17β-oestradiol;β-estradiol;Estradiol-17b;Estradiol-17βPW_C000098Estdiol3478140427735311179992132122333122122707124124884135125295118126501297126845299128072205128453388143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium744.4129744.083277073-2.2791-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-3FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP183819137685780108241883921611291617494685314796144801145308111579010860171476132159627335677811770691887105163715220572061607317213734621075622127589170819722582201518419224118111981189721112008222121521641224928612597226126502494234431543745322769132937716413277384331773963327746113077515115776243367781433477870112807131191131659412010640712042940512045012212060440812061812312114212512127742912140112412148538312306337612308413512322937412324344712371313612384846412396011812404339812547348112569429712574348212621529912652849512701020612722550212757038812810039023716a-HydroxyestroneHMDB0000335Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.566-76-7C05300115116776103012[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3C18H22O3InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1WPOCIZJTELRQMF-QFXBJFAPSA-N(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one286.3655286.15689457-3.792(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one00FDB02195916 alpha-hydroxyestrone;16a-hydroxyestrone;3,16a-dihydroxy-1,3,5(10)-estratrien-17-one;3,16a-dihydroxy-estra-1,3,5(10)-trien-17-one;Estra-1,3,5(10)-triene-3,16a-diol-17-one;16 alpha ohe;3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one;3,16alpha-dihydroxyestra-1,3,5(10)-trien-17-one;Estra-1,3,5(10)-triene-3,16alpha-diol-17-one;16 a ohe;16 α ohe;16α-hydroxyestrone;3,16α-dihydroxy-1,3,5(10)-estratrien-17-one;3,16a-dihydroxyestra-1,3,5(10)-trien-17-one;3,16α-dihydroxyestra-1,3,5(10)-trien-17-one;Estra-1,3,5(10)-triene-3,16α-diol-17-onePW_C000237AOHE433944979994331122708383125296398126846495128454390100EstriolHMDB0000153Estriol is a metabolite of estrone metabolized via 16alpha-hydroxyestrone through the enzyme 16alpha-hydroxysteroid dehydrogenase (EC 1.1.1.147) or to 2- or 4-hydroxyestrone (catechol estrogens) by the action of catecho-O-methyltransferase (EC 2.1.1.6). The latter metabolites can be formed in the brain and may compete with receptors for catecholamines. Metabolites are conjugated with sulfate or glucuronide before excretion by the kidney. During pregnancy, estriol constitutes 60-70% of the total estrogens, increasing to 300-500-fold in relation to non-pregnant women. The late term human fetus produces relatively large amounts of 16 alphahydroxy DHEA, which serves the mother as a precursor of estriol. It has been shown that 90% of the precursors for the formation of estriol are of fetal origin. If abnormal maternal serum screening results, specifically low levels of unconjugated estriol in the second trimester are detected, a diagnosis of Smith-Lemli-Opitz syndrome (SLOS),or RSH is suspected. SLOS is an autosomal recessive disorder caused by mutations of the gene encoding 7-dehydrocholesterol reductase (EC 1.3.1.21, DHCR7). (PMID: 16202579, 16112271, 16097001).50-27-1C051415756279745553DB04573[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3C18H24O3InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1PROQIPRRNZUXQM-ZXXIGWHRSA-N(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol288.3814288.172544634-3.383(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol00DBMET00492FDB00678116a,17b-estriol;13b-methyl-1,3,5(10)-gonatriene-3,16a,17b-triol;16-alpha,17-beta-estriol;16-alpha,17-beta-oestriol;16-alpha-hydroxyestradiol;16a-estriol;16a-hydroxyestradiol;16alpha,17beta-estriol;16alpha,17beta-oestriol;16alpha-hydroxy-17beta-estradiol;16alpha-hydroxyestradiol;16alpha-hydroxyoestradiol;3,16a,17b-estriol;3,16a,17b-trihydroxyestra-1,3,5(10)-triene;3,16alpha,17beta-trihydroxy-1,3,5(10)-estratriene;3,16alpha,17beta-trihydroxyestra-1,3,5(10)-triene;Aacifemine;Colpogyn;Colpovister;Destriol;Deuslon a;Deuslon-a;Estra-1,3,5(10)-triene-3,16a,17b-triol;Estratriol;Estriel;Estriol;Follicular hormone hydrate;Gynasan;Hemostyptanon;Holin v;Hormomed;Incurin;Klimax e;Klimoral;Oekolp;Oestratriol;Oestriol;Oestriolum;Orestin;Orgastyptin;Ortho-gynest;Ovesterin;Ovestin;Ovestinon;Ovestrion;Ovo-vinces;Theelol;Tridestrin;Trihydroxyestrin;Triovex;(16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol;1,3,5(10)-estratriene-3,16-alpha,17beta-triol;3,16alpha,17beta-trihydroxy-delta(1,3,5)-estratriene;(16a,17b)-estra-1,3,5(10)-triene-3,16,17-triol;(16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol;1,3,5(10)-estratriene-3,16-a,17b-triol;1,3,5(10)-estratriene-3,16-α,17β-triol;16α-hydroxyestradiol;3,16a,17b-trihydroxy-delta(1,3,5)-estratriene;3,16α,17β-trihydroxy-δ(1,3,5)-estratriene;3,16a,17b-trihydroxy-δ(1,3,5)-estratrienePW_C000100Estriol43398279996132122709124125298118126848299128456388339Estrogen sulfotransferaseP49888Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
HMDBP00346SULT1E14q13.1U2051512.8.2.4125283914264897315202974337821443Cytochrome P450 1A1P04798Cytochromes 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.
HMDBP01555CYP1A115q24.1AK22311311.14.14.1305624338049266Catechol O-methyltransferaseP21964Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
HMDBP00272COMT22q11.21BC01193512.1.1.64502246841013707239413707485738DnaJ 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 29P30040ERP29BC1014931326223698293878939002644453144606044911845291051919542295491354861135697615135999332792Estradiol 17-beta-dehydrogenase 1P14061Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
HMDBP00847HSD17B117q11-q21CH47115211.1.1.623488140521442Cytochrome 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.
HMDBP01554CYP3A57q21.1CH23695611.14.14.1293429327323369263436104044314590184339549135699615136001332350Estrogen sulfotransferase1PW_P0003503713392753Cytochrome P450 1A11PW_P00075384814431336179911075Catechol O-methyltransferase1PW_P001075123526614394231807UDP-glucuronosyltransferase 1-11PW_P00080791257381913573919145740191557411916574219175743191857441919477619205745192146519225746139Estradiol 17-beta-dehydrogenase 11PW_P00003940792731Cytochrome P450 3A51PW_P000731825144213261799129301045falsePW_R000045Right172941Compoundfalse46558861Compoundfalse17311011Compoundfalse4656431Compoundfalse9293502.8.2.474221PW_R074221Right256285941Compoundfalse256286400341Compoundtrue25628710651Compoundtrue25628811441Compoundtrue2562892441Compoundfalse2562907211Compoundtrue25629114201Compoundtrue6440175374232PW_R074232Right2563369211Compoundtrue2563372441Compoundfalse25633851Compoundfalse2563397491Compoundtrue64412107574239PW_R074239Right25636551Compoundfalse2563667461Compoundtrue25636721421Compoundfalse2563682011Compoundtrue644198072.4.1.17564PW_R000564Right2358941Compoundfalse23597461Compoundtrue236021431Compoundfalse23612011Compoundtrue643938072.4.1.1774265PW_R074265Both256478941Compoundfalse2564791461Compoundtrue256480400341Compoundtrue256481981Compoundfalse2564821431Compoundtrue64445391.1.1.6274260PW_R074260Right256455941Compoundfalse256456400341Compoundtrue25645710651Compoundtrue2564581461Compoundtrue2564591431Compoundtrue25646014201Compoundtrue2564612371Compoundfalse6444073174269PW_R074269Both2564952371Compoundfalse25649611441Compoundtrue256497400341Compoundtrue2564981001Compoundfalse2564997211Compoundtrue644493974253PW_R074253Right256422981Compoundfalse256423400341Compoundtrue25642410651Compoundtrue2564251461Compoundtrue2564261431Compoundtrue25642714201Compoundtrue2564281001Compoundfalse6443373185576794281false251125410regular20019085576888623false60619410regular100110855769110123false100634410regular1001108557704323false95617910regular100120855771400344955false64261810regular787885577210654965false65752110regular787885577311444960false66171910regular5030855774244493false103674610regular1001108557757214959false96172110regular503085577614204949false94762110regular78788557771799499false78675010regular1002585592492123false111148610regular100110855925523false153674110regular10011085592674923false146149110regular10011085592742329false128664810regular10025856075746493false161157110regular1001308560762142493false206173810regular100120856077201493false196158810regular100110856188746493false60190410regular1001308561892143493false1001107910regular100110856190201493false95192410regular100110856331146262false198149410regular503085633240034255false448144510regular78788563339823false302174910regular100100856334143261false197168410regular5030856461400344955false1192149310regular787885646210654965false1177139610regular78788564631464962false1196126910regular50308564641434961false1501126910regular503085646514204949false1497139910regular7878856466237493false2141129210regular1001108564671799499false1326130010regular100258565301144260false2288144710regular503085653140034255false2363140810regular787885653210023false2142173210regular100100856533721259false2287164210regular5030856630400344955false1178162310regular787885663110654965false1178185110regular78788566321464962false1197171910regular50308566331434961false1502171910regular503085663414204949false1498161910regular78788566351799499false1327174810regular1002537787733926false7563618subunitregular1608037787814434999false7617658subunitregular1507037794426622false12616638subunitregular150703780125738492true17513918subunitregular150703780135739492true17514518subunitregular150703780145740492true17515118subunitregular150703780155741492true17515718subunitregular150703780165742492true17516318subunitregular150703780175743492true17516918subunitregular150703780185744492true17517518subunitregular150703780194776492true17518118subunitregular150703780205745492true17518718subunitregular15070378021465492true17519318subunitregular15070378022574649247false17567168proteinregular1751553780735738492true5015198subunitregular150703780745739492true5015798subunitregular150703780755740492true5016398subunitregular150703780765741492true5016998subunitregular150703780775742492true5017598subunitregular150703780785743492true5018198subunitregular150703780795744492true5018798subunitregular150703780804776492true5019398subunitregular150703780815745492true5019998subunitregular15070378082465492true50110598subunitregular15070378083574649247false74610548proteinregular17515537814879222false27915668subunitregular1507037821014424999false130113158subunitregular1507037823879222false211915248subunitregular1507037828214424999false130217638subunitregular15070268936350315312377023377877268937753315314937702437787856418557771213609Cofactor268999107531531237709037794456428559271213815Cofactor2690628073153149377158378012377159378013377160378014377161378015377162378016377163378017377164378018377165378019377166378020377167378021377168378022269109807315314937721937807337722037807437722137807537722237807637722337807737722437807837722537807937722637808037722737808137722837808237722937808326917039315312377294378148269228731315314937735637821056438564671214565Cofactor26925439315312377384378238269295731315314937742837828256448566351214796Cofactor1213598M451 1349 C481 1349 519 1350 549 1350 C550 1319 551 422 550 400 C573 400 730 401 756 401 5false181213599M706 249 C706 327 726 401 756 401 5false181213600M1006 399 C976 399 946 401 916 401 5false18trueM 431.94685504416486 804.261556296296 L 417 803 L 423.38088772118584 816.5751343230784false1213601M956 239 C957 341 946 401 916 401 5false18trueM 431.94685504416486 804.261556296296 L 417 803 L 423.38088772118584 816.5751343230784false1213602M451 1349 C481 1349 520 1347 550 1347 C551 1322 551 821 551 799 C571 799 733 800 761 800 5false181213603M720 657 C719 752 731 800 761 800 5false181213604M735 560 C737 636 731 800 761 800 5false181213605M711 734 C711 786 731 800 761 800 5false181213606M1036 801 C1006 801 941 800 911 800 5false18trueM 492.94685504416486 663.261556296296 L 478 662 L 484.38088772118584 675.5751343230784false1213607M961 736 C962 778 941 800 911 800 5false18trueM 492.94685504416486 663.261556296296 L 478 662 L 484.38088772118584 675.5751343230784false1213608M947 660 C950 724 941 800 911 800 5false18trueM 492.94685504416486 663.261556296296 L 478 662 L 484.38088772118584 675.5751343230784false1213609M521 745.5 L521 795.5 L571 745.5 z10true181213811M1211 541 C1213 673 1231 698 1261 698 5false181213812M1136 801 C1155 801 1182 801 1201 800 C1201 779 1201 718 1201 698 C1221 697 1243 698 1261 698 5false181213813M1536 796 C1516 797 1490 795 1471 796 C1470 775 1472 717 1471 697 C1451 698 1432 698 1411 698 5false18trueM 800.9468550441649 559.261556296296 L 786 558 L 792.3808877211858 571.5751343230784false1213814M1461 546 C1461 671 1441 698 1411 698 5false18trueM 800.9468550441649 559.261556296296 L 786 558 L 792.3808877211858 571.5751343230784false1213815M1296 688.5 L1296 738.5 L1346 688.5 z10true181214019M1636 796 C1666 796 1731 796 1761 796 5false181214020M1711 636 C1709 719 1731 796 1761 796 5false181214021M2061 798 C2031 798 1961 796 1931 796 5false18trueM 1366.9468550441647 668.261556296296 L 1352 667 L 1358.380887721186 680.5751343230784false1214022M1961 643 C1964 731 1961 796 1931 796 5false18trueM 1366.9468550441647 668.261556296296 L 1352 667 L 1358.380887721186 680.5751343230784false1214172M451 1349 C481 1349 530 1347 551 1347 C550 1326 550 1157 550 1134 C571 1133 716 1133 751 1134 5false181214173M701 969 C702 1066 721 1134 751 1134 5false181214174M1001 1134 C971 1134 951 1134 921 1134 5false18trueM 469.94685504416486 769.261556296296 L 455 768 L 461.38088772118584 781.5751343230784false1214175M951 979 C952 1064 951 1134 921 1134 5false18trueM 469.94685504416486 769.261556296296 L 455 768 L 461.38088772118584 781.5751343230784false1214372M351 1444 C350 1465 354 1536 354 1566 5false18trueM 404.94685504416486 1169.261556296296 L 390 1168 L 396.38088772118584 1181.5751343230784false1214373M223 1524 C278 1523 354 1536 354 1566 5false18trueM 404.94685504416486 1169.261556296296 L 390 1168 L 396.38088772118584 1181.5751343230784false1214376M487 1523 C431 1522 354 1536 354 1566 5false18trueM 404.94685504416486 1169.261556296296 L 390 1168 L 396.38088772118584 1181.5751343230784false1214379M352 1749 C352 1719 354 1666 354 1636 5false18trueM 404.94685504416486 1169.261556296296 L 390 1168 L 396.38088772118584 1181.5751343230784false1214380M222 1684 C285 1683 354 1666 354 1636 5false18trueM 404.94685504416486 1169.261556296296 L 390 1168 L 396.38088772118584 1181.5751343230784false1214558M451 1349 C481 1349 1271 1350 1301 1350 5false181214559M1270 1532 C1270 1463 1271 1350 1301 1350 5false181214560M1255 1435 C1254 1391 1271 1350 1301 1350 5false181214561M1250 1284 C1251 1324 1271 1350 1301 1350 5false181214562M1501 1284 C1503 1330 1481 1350 1451 1350 5false18trueM 302.94685504416486 1386.261556296296 L 288 1385 L 294.38088772118584 1398.5751343230784false1214563M1497 1438 C1500 1398 1481 1350 1451 1350 5false18trueM 302.94685504416486 1386.261556296296 L 288 1385 L 294.38088772118584 1398.5751343230784false1214564M2141 1347 C2111 1347 1481 1350 1451 1350 5false18trueM 302.94685504416486 1386.261556296296 L 288 1385 L 294.38088772118584 1398.5751343230784false1214565M521 1160.5 L521 1210.5 L571 1160.5 z10true181214652M2191 1402 C2191 1432 2194 1494 2194 1524 5false18trueM 561.9468550441649 1369.261556296296 L 547 1368 L 553.3808877211858 1381.5751343230784false1214653M2313 1477 C2257 1475 2194 1494 2194 1524 5false18trueM 561.9468550441649 1369.261556296296 L 547 1368 L 553.3808877211858 1381.5751343230784false1214655M2402 1486 C2349 1487 2194 1494 2194 1524 5false18trueM 561.9468550441649 1369.261556296296 L 547 1368 L 553.3808877211858 1381.5751343230784false1214656M2192 1732 C2192 1702 2194 1624 2194 1594 5false18trueM 561.9468550441649 1369.261556296296 L 547 1368 L 553.3808877211858 1381.5751343230784false1214657M2312 1642 C2262 1643 2194 1624 2194 1594 5false18trueM 561.9468550441649 1369.261556296296 L 547 1368 L 553.3808877211858 1381.5751343230784false1214789M402 1799 C432 1799 1272 1798 1302 1798 5false181214790M1256 1662 C1256 1720 1272 1798 1302 1798 5false181214791M1256 1890 C1252 1843 1272 1798 1302 1798 5false181214792M1251 1734 C1250 1785 1272 1798 1302 1798 5false181214793M1502 1734 C1502 1795 1482 1798 1452 1798 5false18trueM 449.94685504416486 1494.261556296296 L 435 1493 L 441.38088772118584 1506.5751343230784false1214794M1498 1658 C1500 1717 1482 1798 1452 1798 5false18trueM 449.94685504416486 1494.261556296296 L 435 1493 L 441.38088772118584 1506.5751343230784false1214795M2142 1782 C2112 1782 1482 1798 1452 1798 5false18trueM 449.94685504416486 1494.261556296296 L 435 1493 L 441.38088772118584 1506.5751343230784false1214796M772 1628 L772 1678 L822 1628 z10true182785503153145210877848557671213598Left10877858557681213599Left10877868557691213600Right10877878557701213601Right23762692926893627855131531742214910877888557671213602Left10877898557711213603Left10877908557721213604Left10877918557731213605Left10877928557741213606Right10877938557751213607Right10877948557761213608Right237627644012689372785973153174232210879758559241213811Left10879768557741213812Left10879778559251213813Right10879788559261213814Right2376736441226899927864431531742394910881628559251214019Left10881638560751214020Left10881648560761214021Right10881658560771214022Right23772064419269062278679315315644910883008557671214172Left10883018561881214173Left10883028561891214174Right10883038561901214175Right237755643932691092787243153174265210884818557671214372Left10884828563311214373Left10884838563321214376Left10884848563331214379Right10884858563341214380Right2378006444526917027876631531742604910886478557671214558Left10886488564611214559Left10886498564621214560Left10886508564631214561Left10886518564641214562Right10886528564651214563Right10886538564661214564Right237842644402692282787863153174269210887308564661214652Left10887318565301214653Left10887328565311214655Left10887338565321214656Right10887348565331214657Right2378626444926925427881731531742534910888568563331214789Left10888578566301214790Left10888588566311214791Left10888598566321214792Left10888608566331214793Right10888618566341214794Right10888628565321214795Right237893644332692955826119406631.01.0-90290484497119215M555 899 C555 849 605 799 655 799 C1056 799 1576 799 1977 799 C2027 799 2077 849 2077 899 C2077 1140 2077 1452 2077 1693 C2077 1743 2027 1793 1977 1793 C1576 1793 1056 1793 655 1793 C605 1793 555 1743 555 1693 C555 1452 555 1140 555 899 91true61522.0994.0119230M579 1147 C626 1147 2011 1146 2053 1147 91false61474.00.0119243M579 1347 C628 1348 2012 1349 2053 1350 91false61474.03.0119248M125 225 C125 175 175 125 225 125 C888 125 1750 125 2413 125 C2463 125 2513 175 2513 225 C2513 732 2513 1392 2513 1899 C2513 1949 2463 1999 2413 1999 C1750 1999 888 1999 225 1999 C175 1999 125 1949 125 1899 C125 1392 125 732 125 225 1true62388.01874.010140915Cytosol207188201.01.01601510141015Endoplasmic Reticulum Membrane18621105201.01.016015573331991358529773210318194#FFEEDE415741046