9337Context3-beta-Hydroxysteroid Dehydrogenase Deficiency3-beta (β)-hydroxysteroid dehydrogenase (HSD) deficiency is an inherited disorder that affects hormone-producing glands including the gonads (ovaries in females and testes in males) and the adrenal glands.Mutations in the HSD3B2 gene cause 3β-HSD deficiency. The HSD3B2 gene provides instructions for making the 3β-HSD enzyme. This enzyme is found in the gonads and adrenal glands. The 3β-HSD enzyme is involved in the production of many hormones, including cortisol, aldosterone, androgens, and estrogen. Cortisol has numerous functions such as maintaining energy and blood sugar levels, protecting the body from stress, and suppressing inflammation.DiseasePW122130CenterPathwayVisualizationContext12240645004500#000099PathwayVisualization8810688232SteroidogenesisSteroidogenesis is the process wherein desired forms of steroids are generated by transformation of other steroids. Products of steroidogenesis include androgens, testosterone, estrogens and progesterone, corticoids, cortisol and aldosterone. The first step in the synthesis of all steroid hormones is the synthesis of pregnenolone from cholesterol. In this process, cholesterol mobilized from cytosolic lipid droplets or from lysosomes is transported to mitochondria and becomes localized to the inner mitochondrial membrane. In the inner mitochondrial membrane, cholesterol is converted to pregnenolone in a sequence of three reactions, all catalyzed by CYP11A (side chain cleavage enzyme). Finally, pregnenolone re-enters the cytosol. Aldosterone, the major human mineralocorticoid, is synthesized in the zona glomerulosa of the adrenal cortex from pregnenolone. Pregnenolone is converted to progesterone in two reactions, both catalyzed by 3-beta-hydroxysteroid dehydrogenase/isomerase. Progesterone is hydroxylated by CYP21A2 to form deoxycorticosterone, which in turn is converted to aldosterone in a three-reaction sequence catalyzed by CYP11B2. Cortisol, the major human glucocorticoid, is synthesized in the zona fasciculata of the adrenal cortex from pregnenolone. Pregnenolone is converted to 17alpha-hydoxyprogesterone in two reactions, both catalyzed by 3-beta-hydroxysteroid dehydrogenase/isomerase. 17Alpha-hydroxyprogesterone is hydroxylated by CYP21A2 to form 11-deoxycortisol, which in turn is converted to cortisol by CYP11B1. The conversion of the active steroid hormone, cortisol, to inactive cortisone occurs in many tissues, notably the liver. Testosterone biosynthesis begins with pregnenolone. Subsequent steps require several enzymes including, 3β-hydroxysteroid dehydrogenase, 17α-hydroxylase/C17-20-lyase and 17β-hydroxysteroid dehydrogenase type 3. Specifically, pregnenolone is converted to 17-hydroxypregnenolone and dehydroepiandrosterone by CYP17 (17α-hydroxylase). Dehydroepiandrosterone is then converted to androstenedione by 3β-hydroxysteroid dehydrogenase. Androstenedione can have two fates, it can either be converted to estrone via CYP19 (aromatase/estrogen synthase) or it can be converted to testosterone via 17β-hydroxysteroid dehydrogenase. Free testosterone is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. Testosterone may also be converted to estradiol by the action of CYP19 (aromatase/estrogen synthase).Metabolic1710862285SubPathway10775847Compound1191CellCL:00000004Cardiomyocyte CL:00007462Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote10Drosophila melanogaster7227EukaryoteFruit fly49Bathymodiolus platifrons220390EukaryoteDeep sea mussel2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia45CytoplasmGO:00057372MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:00057894PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057831CytosolGO:000582910Cell MembraneGO:000588619sarcoplasmic reticulumGO:001652935ChloroplastGO:00095073Mitochondrial MatrixGO:000575936MembraneGO:001602015NucleusGO:00056346LysosomeGO:000576416Lysosomal LumenGO:004320211Extracellular SpaceGO:000561518Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575812Mitochondrial Inner MembraneGO:000574325Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520231Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579032Inner MembraneGO:00702589Smooth Endoplasmic Reticulum LumenGO:00482381LiverBTO:00007597295cardiocyteBTO:00015392Endothelium BTO:00003934Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273108511PW_BS0000081115121PW_BS000111122551PW_BS0001221355171PW_BS0001353211PW_BS000003101711PW_BS0000105411PW_BS000005181311PW_BS0000182111PW_BS00000229111PW_BS00002949711PW_BS000049311511PW_BS00003114101PW_BS00001410813PW_BS0001081471241PW_BS00014715924PW_BS0001593551914PW_BS000035117131PW_BS000117188118PW_BS0000241632181PW_BS000163205561PW_BS0000241601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS0001702253541PW_BS000024151141PW_BS000151224241PW_BS0000241985181PW_BS0000242111018PW_BS000024222341PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS000024315123PW_BS0000243221231PW_BS00002429341PW_BS0000241321121PW_BS0001323317121PW_BS00002833217121PW_BS00002813013121PW_BS0001301122121PW_BS0001121151012PW_BS0001153361121PW_BS0000281192171PW_BS000119943PW_BS000094407251PW_BS000115405105PW_BS0001151231751PW_BS0001231251351PW_BS000125429151PW_BS000115124151PW_BS000124383751PW_BS0001003761017PW_BS00005344717171PW_BS00011513613171PW_BS0001364641171PW_BS0001151181171PW_BS0001183987171PW_BS0001134812101PW_BS0001152975101PW_BS0000242991101PW_BS0000244957101PW_BS000115206261PW_BS000024388161PW_BS000112390761PW_BS0001123344121PW_BS000028408451PW_BS0001153744171PW_BS0000534824101PW_BS000115502461PW_BS000115231511PW_BS000023711PW_BS0000079611PW_BS00000916212PW_BS0000162811611PW_BS000028204111PW_BS00002015111PW_BS0000154311PW_BS000004331811PW_BS0000332441011PW_BS000024221411PW_BS000022422411PW_BS00004213121PW_BS000013126651PW_BS00012612711651PW_BS0001272164181PW_BS0000242156181PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS00002430013101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS000024171211PW_BS0000172941141PW_BS00002413412121PW_BS0001341136121PW_BS000113337116121PW_BS00002812915121PW_BS00012934141121PW_BS0000281141112PW_BS0001141333121PW_BS00013332914121PW_BS00002834524121PW_BS00002834318121PW_BS000028360410121PW_BS0000284141551PW_BS000115409115PW_BS000115406351PW_BS0001154151851PW_BS00011543441051PW_BS0001153821451PW_BS0001004182451PW_BS0001153841251PW_BS0001004436171PW_BS000115448116171PW_BS00011545015171PW_BS0001151371117PW_BS0001371203171PW_BS00012045118171PW_BS000115469410171PW_BS00011539914171PW_BS00011345424171PW_BS00011512112171PW_BS0001214781010PW_BS0001154831110PW_BS0001154793101PW_BS00011548414101PW_BS00011548924101PW_BS00011548012101PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS000024501361PW_BS0001155041861PW_BS00011551541061PW_BS0001153891461PW_BS0001123951361PW_BS0001135062461PW_BS0001153911261PW_BS000112541315PW_BS000054432511PW_BS00004360251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027971521PW_BS000097100521PW_BS000100103331PW_BS000103105113PW_BS000105110231PW_BS0001106131PW_BS000006140103PW_BS000140101531PW_BS00010114315191PW_BS0001431465191PW_BS000146107313PW_BS000107951721PW_BS0000951553241PW_BS0001551572241PW_BS0001571613181PW_BS00016111PW_BS00000116611PW_BS0001661783211PW_BS0001781802211PW_BS00018015284PW_BS00015221425181PW_BS0000241901118PW_BS00002416212181PW_BS000162261115PW_BS0000262771218PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000243081011PW_BS0000243183123PW_BS000024253541PW_BS0000243331212PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS0000283683601PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154251355PW_BS0001154192551PW_BS000115436255PW_BS0001154461217PW_BS00011546013175PW_BS00011545525171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155072561PW_BS0001155131761PW_BS000115111811PW_BS00001114117191PW_BS00014178811PW_BS0000781873118PW_BS000024219314PW_BS00002422014PW_BS0000241951318PW_BS0000243125231PW_BS0000243201123PW_BS00002432711125PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS0001094241155PW_BS00011545911175PW_BS000115121911PW_BS000012290711b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-alHMDB000675411beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is converted from Aldosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC:1.3.99.6). It is then converted to 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC:1.1.1.50).C0547353477896[H][C@@]12CCC(C(=O)CO)C1(CC(O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C)C=OC21H32O5InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h11-17,19,22,24-25H,2-10H2,1H3/t12-,13-,14+,15+,16?,17?,19-,20+,21?/m1/s1YWTDWORQGPLRLL-SXWUTGHTSA-N(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde364.4758364.224974134-3.333(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde00FDB02405811beta,21-dihydroxy-3,20-oxo-5beta-pregnan-18-al;Not availablePW_C002907NA2172878959111121798122124349135146NADPHHMDB0000221Nicotinamide 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_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139029063a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-alHMDB00067533alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al is an intermediate in C21-Steroid hormone metabolism. 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al is converted from 11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).C05474440695389571CC12CC[C@@H](O)CC1CCC1C3CCC(C(=O)CO)C3(CC(O)C21)C=OC21H32O5InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h11-17,19,22,24-25H,2-10H2,1H3/t12?,13-,14?,15?,16?,17?,19?,20?,21?/m1/s1YWTDWORQGPLRLL-NDCWLUSSSA-N(5R)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde364.4758364.224974134-3.333(5R)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde00FDB0240573alpha,11beta,21-trihydroxy-20-oxo-5beta-pregnan-18-al;Not availablePW_C002906T20OPal2173878960111121799122124350135143NADPHMDB0000217Nicotinamide 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_C000143NADP183819137685780108241883921611291617494685314796144801145308111579010860171476132159627335677811770691887105163715220572061607317213734621075622127589170819722582201518419224118111981189721112008222121521641224928612597226126502494234431543745322769132937716413277384331773963327746113077515115776243367781433477870112807131191131659412010640712042940512045012212060440812061812312114212512127742912140112412148538312306337612308413512322937412324344712371313612384846412396011812404339812547348112569429712574348212621529912652849512701020612722550212757038812810039026AldosteroneHMDB0000037Aldosterone is a steroid hormone produced by the adrenal cortex in the adrenal gland to regulate sodium and potassium balance in the blood. Specifically it regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium. It is synthesized from cholesterol by aldosterone synthase, which is absent in other sections of the adrenal gland. It is the sole endogenous member of the class of mineralocorticoids. Aldosterone increases the permeability of the apical (luminal) membrane of the kidney's collecting ducts to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis, reabsorbing sodium (Na+) ions and water into the blood, and excreting potassium (K+) ions into the urine.52-39-1C017802475842527584ALDOSTERONE24774738C[C@]12CCC(=O)C=C1CCC1C3CC[C@H](C(=O)CO)[C@]3(C[C@H](O)C21)C=OC21H28O5InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14?,15?,16-,17+,19?,20+,21-/m1/s1PQSUYGKTWSAVDQ-SRPWZAMTSA-N(2R,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde360.444360.193674006-3.392(2R,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde00FDB021883(+)-aldosterone;(11b)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al;(11beta)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al;11,21-dihydroxy-3,20-dioxopregn-4-en-18-al;11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-13-carbaldehyde;11b,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al;11beta,21-dihydroxy-3,20-diketo-4-pregnen-18-al;11beta,21-dihydroxy-3,20-diketopregn-4-ene-18-al;11beta,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al;11beta,21-dihydroxypregn-4-ene-3,18,20-trione;18-formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione;18-oxocorticosterone;Aldocorten;Aldocortene;Aldocortin;Aldosterone;Aldosteronum;D-aldosterone;Electrocortin;Elektrocortin;Reichstein x;Delta-aldosteronePW_C000026Aldostr21748265423296277896111112180012212435213522318-HydroxycorticosteroneHMDB000031918-Hydroxycorticosterone is a corticosteroid and a derivative of corticosterone. If it is present in sufficiently high concentrations, it can lead to serious electrolyte imbalances (an electrolyte toxin). 18-Hydroxycorticosterone serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa. Chronically high levels of 18-hydroxycorticosterone are associated with at least three inborn errors of metabolism including adrenal hyperplasia type V, corticosterone methyl oxidase I deficiency, and corticosterone methyl oxidase II deficiency. Each of these conditions is characterized by excessive amounts of sodium being released in the urine (salt wasting), along with insufficient release of potassium in the urine, usually beginning in the first few weeks of life. This imbalance leads to low levels of sodium and high levels of potassium in the blood (hyponatremia and hyperkalemia, respectively). Individuals with corticosterone methyloxidase deficiency can also have high levels of acid in the blood (metabolic acidosis). Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). The hyponatremia, hyperkalemia, and metabolic acidosis associated with corticosterone methyloxidase deficiency can cause nausea, vomiting, dehydration, low blood pressure, extreme tiredness (fatigue), and muscle weakness.561-65-9C01124112221648510748[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(CO)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O5InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1HFSXHZZDNDGLQN-ZVIOFETBSA-N(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one362.4599362.20932407-3.383(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02194511b,18,21-trihydroxy-pregn-4-ene-3,20-dione;18-hydroxycorticosterone;11-hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-onePW_C00022318-HCC21793789621121218014071243541191065OxygenHMDB0001377Oxygen 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_C001065O2959110524516500185058549146252863836491067431688207541576347693383621375492016242531222803294260424747135467123548012554931265508127580910859731476129159700618870321637050160731921375332107560212839515111816216118641981188321511894211120572251206316412247286122792261232524912706291127162921300429813016300130263011303830213260223422761742657315769102937704429477214134773501117736313077377331773953327749711377512115775373347762633677723337777361127774712977756341778051147781213378070329781511327838134578805343791113601200474081203831221204264051205424071205534141205944091206014061208834151210451241211043831216054341216564291221173821225734181226893841227983741228224431230271351230603761231284471231391361231634481231761191231874501232191371232261201234594511236091181236693981241634691242144641246693991251454541252751211254254821257064781257314831257372971257404791258844811261002991262724841265224951267214891268254801269645021269862071271982091272142081272192051272225011273055041273452061275573881275745151278353891280813951280953901283125061284323911420WaterHMDB0002111Water 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_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911190CorticosteroneHMDB0001547Corticosterone, also known as 17-deoxycortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, corticosterone is considered to be a steroid lipid molecule. Corticosterone exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Corticosterone has been found throughout most human tissues, and has also been detected in multiple biofluids, such as blood and urine. Within the cell, corticosterone is primarily located in the cytoplasm, membrane (predicted from logP), mitochondria and endoplasmic reticulum. In humans, corticosterone is involved in the steroidogenesis pathway. Corticosterone is also involved in several metabolic disorders, some of which include 21-hydroxylase deficiency (cyp21), 3-Beta-hydroxysteroid dehydrogenase deficiency, 11-beta-hydroxylase deficiency (cyp11b1), and adrenal hyperplasia type 5 or congenital adrenal hyperplasia due to 17 Alpha-hydroxylase deficiency. Corticosterone is an adrenocortical steroid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. (From Goodman and Gilman\'s The Pharmacological Basis of Therapeutics, 8th ed, p1437).50-22-6C021405753168275550DB04652[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]12C)C(=O)COC21H30O4InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1OMFXVFTZEKFJBZ-HJTSIMOOSA-N(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one346.4605346.214409448-3.882(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02268411,21-dihydroxypregn-4-ene-3,20-dione;11,21-dihydroxyprogesterone;11-hydroxycorticoaldosterone;17-deoxycortisol;4-pregnene-11 corticosteron;Corticosterone;Kendall's compound b;Reichstein's substance h;(11beta)-11,21-dihydroxypregn-4-ene-3,20-dione;11beta,21-dihydroxy-4-pregnene-3,20-dione;11beta,21-dihydroxyprogesterone;(11b)-11,21-dihydroxypregn-4-ene-3,20-dione;(11β)-11,21-dihydroxypregn-4-ene-3,20-dione;11b,21-dihydroxy-4-pregnene-3,20-dione;11β,21-dihydroxy-4-pregnene-3,20-dione;11b,21-dihydroxyprogesterone;11β,21-dihydroxyprogesteronePW_C001190Cortcos2182378965112121803407124356119291011b,21-Dihydroxy-5b-pregnane-3,20-dioneHMDB000675711beta,21-Dihydroxy-5beta-pregnane-3,20-dione is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-5beta-pregnane-3,20-dione is the 3rd to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from Corticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to Tetrahydrocorticosterone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).566-01-8C05475 4426333924850104[H][C@@]12CCC(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12CC21H32O4InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-17,19,22,24H,3-11H2,1-2H3/t12-,14+,15+,16?,17+,19-,20+,21+/m1/s1CTTOFMJLOGMZRN-MGXYISIMSA-N(1S,2S,7R,10S,11S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one348.4764348.230059512-3.682(1S,2S,7R,10S,11S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one00FDB02406111beta,21-dihydroxy-5beta-pregnane-3,20-dione;5beta-pregnane-11beta,21-diol-3,20-dionePW_C00291011B21D52188878967111121804122124357135183TetrahydrocorticosteroneHMDB0000268Tetrahydrocorticosterone is one of the major urinary metabolites from corticosterone. Premenopausal patients with early breast cancer excrete subnormal amounts of tetrahydrocorticosterone as compared with the normal subjects of corresponding ages. (PMID 1133844).68-42-8C0547698632458038941[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])C2CC[C@]2([H])C[C@H](O)CC[C@]12CC21H34O4InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13-,14?,15+,16-,17+,19-,20+,21+/m1/s1RHQQHZQUAMFINJ-DSCSGEDNSA-N1-[(1S,2S,5R,7R,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one350.4923350.245709576-3.4731-[(1S,2S,5R,7R,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethanone00FDB021923(3a,5b,11b)-3,11,21-trihydroxy-pregnan-20-one;3a,11b,21-trihydroxy-5b-pregnan-20-one;3a,5b-tetrahydrocorticosterone;5b-pregnane-3a,11b,21-triol-20-one;Tetrahydro-corticosterone;TetrahydrocorticosteronePW_C000183Tetrahy2195878968111121805122124358135202811-DehydrocorticosteroneHMDB000402911-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.).72-23-1C054901378344924850107[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H28O4InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1FUFLCEKSBBHCMO-IWBQTIMDSA-N(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione344.4446344.198759384-3.86111-dehydrocorticosterone00FDB02328211-dehydro-corticosterone;11-dehydrocorticosteron;11-dehydrocorticosterone;11-oxo-11-deoxycorticosterone;11-oxocorticosterone;17-(1-keto-2-hydroxyethyl)-d4-androsten-3,11-dione;17-deoxycortisone;21-hydroxypregn-4-ene-3,11,20-trione;21-hydroxypregn-4-ene-3,11-20-trione;4-pregnen-21-ol-3,11,20-trione;D4-pregnen-21-ol-3,11,20-trione;D4-pregnene-21-ol-3,11,20-trione;Dehydrocorticosterone;Dehydrocortocicosterone;Kendall's compound aPW_C00202811dhccn22011878969130121806125124359136290921-Hydroxy-5b-pregnane-3,11,20-trioneHMDB000675621-Hydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 21-Hydroxy-5beta-pregnane-3,11,20-trione is the. second to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from 11-Dehydrocorticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).10417-86-4C054774426334524850108[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12CC21H30O4InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1ZDUVZJUTJOBJHS-HNEBDTNWSA-N(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione346.4605346.214409448-3.841(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione00FDB02406021-hydroxy-5beta-pregnane-3,11,20-trionePW_C00290921-Hydr224887897011112180712212436013529083a,21-Dihydroxy-5b-pregnane-11,20-dioneHMDB00067553alpha,21-Dihydroxy-5beta-pregnane-11,20-dione is an intermediate in C21-Steroid hormone metabolism. 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione is converted from Tetrahydrocorticosterone via the enzyme 11beta-hydroxysteroid dehydrogenase (EC 1.1.1.146). It is then converted to 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).566-03-0C054784426334724850110[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12CC21H32O4InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1XWYBFXIUISNTQG-XPYNSANSSA-N(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one348.4764348.230059512-3.742(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one00FDB0240593alpha,21-dihydroxy-5beta-pregnane-11,20-dione;5beta-pregnane-3alpha,21-diol-11,20-dionePW_C002908321D5B2249497897133112180838312436139840034Hydrogen 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+215467087531578831848311162146326146454223149278017425022425442454710457618469470524110353271115353112562610856391075699100572010557421175963147603715560701576093161613015962321666483178660115266921016843188691018771001637168205719120674532197454220747222275252137532210755821275721607590170819522582181518243226841316284202249139195915524911915164120152811218128512246286122662871252122713257223133252941533030842329315423543184240132242405312424543207691229377136133772101347737233177804114779551327799032777991347783793457992913080019368803873108038830480722119938231249482338311055038811285594113280390115537398115539118115856336116205109119973406120193407120549122120593409121170424121171425122569418122615384122687125122758120123183135123218137123742459123743460125141454125188121125273136125359479125550481125730483125736297125809299126517495126717489126766480126823300126902501127213208128308506128361391128430395203011b-HydroxyprogesteroneHMDB000403111beta-Hydroxyprogesterone is a normal human metabolite. Plasma 11beta-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. Increased plasma 11beta-Hydroxyprogesterone levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. 21-hydroxylase deficiency (OMIM 201910) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews. 21-hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. (PMID: 3546944, 2537337). 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells.It activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. Furthermore, 11OHP was unable to activate the mutant hMR/N770A, in which Ala is substituted for Asn at position 770. These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption.600-57-7C0549844263342CPD-27224840621[H][C@@]12CC[C@H](C(O)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC20H28O4InChI=1S/C20H28O4/c1-19-8-7-12(21)9-11(19)3-4-13-14-5-6-15(18(23)24)20(14,2)10-16(22)17(13)19/h9,13-17,22H,3-8,10H2,1-2H3,(H,23,24)/t13-,14-,15+,16+,17+,19-,20-/m0/s1XEFVQCSDIKHROY-CAPFDLLWSA-N(1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-14-carboxylic acid332.4339332.198759384-3.71211b-hydroxyprogesterone0-1FDB023284(11beta)-11-hydroxypregn-4-ene-3,20-dione;11-beta-hydroxypregn-4-ene-3,20-dione;11-beta-hydroxyprogesterone;11b-hydroxyprogesterone;11beta-hydroxyprogesterone;11beta-hydroxypregn-4-ene-3,20-dione;21-deoxycorticosteronePW_C00203011Hprgt22604978973331121810383124363398202921-DeoxycortisolHMDB0004030Plasma 21-deoxycortisol (21DF) is an excellent marker of 21-hydroxylase deficiency. Currently, it is the only marker able to detect heterozygous carriers with 21-hydroxylase deficiency after Adrenocorticotropic Hormone (ACTH) stimulation. The syndrome of congenital adrenal hyperplasia (CAH) comprises the spectrum of autosomal recessive enzymatic disorders that impair cortisol biosynthesis. The hormonal pattern and clinical manifestations result from hyperstimulation of the adrenal cortex by excessive production of ACTH, untied from the negative feedback exerted by reduced cortisol levels, and the ultimate accumulation of F precursors and androgens. These abnormalities predispose the female newborn to ambiguous genitalia (female pseudohermaphroditism) and precocious puberty that may occur in both sexes. CAH due to 21-hydroxylase deficiency (21OHD) comprises nearly 90% of all cases, with an estimated worldwide incidence of 1 in 14,000 live births. Because 21-deoxycortisol (21DF) is an 11b-hydroxylase (11bOH) derivative of 17-hydroxyprogesterone (17OHP), its serum levels are parallel and proportionally elevated in patients with 21OHD but decreased or undetectable in those with 11b-hydroxylase deficiency (11bOHD). Due to the marked buildup of 17OHP in 21OHD, this precursor steroid can proceed directly to 11-hydroxylation, producing distinct elevations of 21DF. (PMID: 16551734, 10731638).641-77-0C05497222803193458[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O4InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-/m0/s1LCZBQMKVFQNSJR-CZUPSRJTSA-N(1S,2R,10S,11S,14R,15S,17R)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one346.4605346.214409448-3.76221-deoxycortisol00FDB02328311b,17-dihydroxy-pregn-4-ene-3,20-dione;11b,17-dihydroxy-progesterone;11b,17a-dihydroxypregn-4-ene-3,20-dione;11b,17a-dihydroxyprogesterone;21-dehydrohydrocortisone;21-deoxycortisol;21-deoxyhydrocortisone;21-desoxycortisol;4-pregnene-11beta,17alpha-diol-3,20-dione;Pregn-4-ene-11b,17a-diol-3,20-dionePW_C00202921HOCrt2262497897433112181238312436539845CortisolHMDB0000063Cortisol is the main glucocorticoid secreted by the adrenal cortex and it is involved in the stress response. Its synthetic counterpart hydrocortisone is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. Hydrocortisone is synthesized from pregnenolone and is used as an immunosuppressive drug given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. Cortisol increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. The amount of cortisol present in the serum undergoes diurnal variation, with the highest levels present in the early morning and lower levels in the evening, several hours after the onset of sleep. Cortisol is found to be associated with ACTH deficiency and glucocorticoid deficiency, which are inborn errors of metabolism. Cortisol binds to the cytosolic glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA-bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically, glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes and prevents phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products of inflammation, prostaglandins and leukotrienes, are inhibited by the action of glucocorticoids. Glucocorticoids also stimulate the escape of lipocortin-1 into the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst, and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines, etc.) from neutrophils, macrophages, and mastocytes. Additionally, the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.50-23-7C007355754176505551DB00741[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O5InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1JYGXADMDTFJGBT-VWUMJDOOSA-N(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one362.4599362.20932407-3.263(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02188811-hydrocortisone;11-beta-hydrocortisone;11-beta-hydroxycortisone;11a-hydroxycorticosterone;11alpha-hydroxycorticosterone;11b,17,21-trihydroxyprogesterone;11b-hydrocortisone;11b-hydroxycortisone;11beta,17,21-trihydroxyprogesterone;11beta-hydrocortisone;11beta-hydroxycortisone;17-hydroxycorticosterone;17a-hydroxycorticosterone;17alpha-hydroxycorticosterone;4-pregnene-11alpha,21-triol 3,20-dione;4-pregnene-11b,17a,21-triol-3,20-dione;Acticort;Aeroseb hc;Aeroseb-hc;Ala-cort;Ala-scalp;Alacort;Algicirtis;Alphaderm;Amberin;Anflam;Anti-inflammatory hormone;Aquacort;Aquanil hc;Barseb hc;Basan-corti;Caldecort spray;Cetacort;Chronocort;Clear aid;Cleiton;Cobadex;Compound f;Cor-tar-quin;Cort-dome;Cort-quin;Cortanal;Cortenema;Cortesal;Corticreme;Cortifan;Cortifoam;Cortiment;Cortisol alcohol;Cortisolonum;Cortisporin;Cortisporin otico;Cortispray;Cortizol;Cortolotion;Cortonema;Cortoxide;Cremesone;Cremicort-h;Cutisol;Delacort;Derm-aid;Dermil;Dermolate;Dihydrocostisone;Dioderm;Dome-cort;Domolene-hc;Drotic;Ef corlin;Efcorbin;Efcortelan;Efcortelin;Eldercort;Epicort;Epiderm h;Esiderm h;Evacort;Ficortril;Fiocortril;Foille insetti;Genacort;Gyno-cortisone;H-cort;Hc;Heb cort;Heb-cort;Hidalone;Hidro-colisona;Hidrocortisona;Hycort;Hycortol;Hycortole;Hydracort;Hydrasson;Hydro-adreson;Hydro-colisona;Hydrocort;Hydrocortal;Hydrocorticosterone;Hydrocortisone;Hydrocortisone alcohol;Hydrocortisone base;Hydrocortisone free alcohol;Hydrocortisonum;Hydrocortistab;Hydrocortisyl;Hydrocortone;Hydroskin;Hydroxycortisone;Hysone;Hytisone;Hytone;Hytone lotion;Idrocortisone;Incortin-h;Incortin-hydrogen;Kendall's compound f;Komed hc;Kyypakkaus;Lacticare hc;Lacticare-hc;Lactisona;Lubricort;Maintasone;Medicort;Meusicort;Mildison;Milliderm;Neo-cort-dome;Neosporin-h ear;Nutracort;Nystaform-hc;Optef;Otalgine;Otic-neo-cort-dome;Otobiotic;Otocort;Otosone-f;Pediotic suspension;Penecort;Permicort;Polcort h;Preparation h hydrocortisone cream;Prepcort;Prestwick_265;Prevex hc;Proctocort;Proctofoam;Protocort;Racet;Rectoid;Reichstein's substance m;Remederm hc;Sanatison;Scalpicin capilar;Schericur;Scheroson f;Sigmacort;Signef;Stiefcorcil;Synacort;Systral hydrocort;Tarcortin;Timocort;Topicort;Transderma h;Traumaide;Uniderm;Vioform-hydrocortisone;Vosol hc;Vytone;ZenoxonePW_C000045HC2274497897533112181438312436739810DeoxycorticosteroneHMDB000001611-Deoxycorticosterone (also called desoxycortone, 21-hydroxyprogesterone, DOC, or simply deoxycorticosterone) is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone. It is classified as a member of the 21-hydroxysteroids. 21-hydroxysteroids are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Deoxycorticosterone is very hydrophobic, practically insoluble (in water), and relatively neutral. Deoxycorticosterone can be synthesized from progesterone by 21-beta-hydroxylase and is then converted to corticosterone by 11-beta-hydroxylase. Corticosterone is then converted to aldosterone by aldosterone synthase. Deoxycorticosterone stimulates the collecting tubules in the kidney to continue to excrete potassium in much the same way that aldosterone does. Deoxycorticosterone has about 1/20 of the sodium retaining power of aldosterone and about 1/5 the potassium excreting power of aldosterone (Wikipedia). Deoxycorticosterone can be found throughout all human tissues and has been detected in amniotic fluid and blood. When present in sufficiently high levels, deoxycorticosterone can act as a hypertensive agent and a metabotoxin. A hypertensive agent increases blood pressure and causes the production of more urine. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxycorticosterone are associated with congenital adrenal hyperplasia (CAH) and with adrenal tumors producing deoxycorticosterone (PMID: 20671982). High levels of this mineralocorticoid are associated with resistant hypertension, which can result in polyuria, polydipsia, increased blood volume, edema, and cardiac enlargement. Deoxycorticosterone can be used to treat adrenal insufficiency. In particular, desoxycorticosterone acetate (DOCA) is used as replacement therapy in Addison's disease.64-85-7C0320561661697311-DEOXYCORTICOSTERONE5932[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O3InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1ZESRJSPZRDMNHY-YFWFAHHUSA-N(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one330.4611330.219494826-4.301(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02187311-dehydroxycorticosterone;11-deoxy-corticosterone;11-deoxycorticosterone;11-desoxycorticosterone;21-hydroxy-3,20-dioxopregn-4-ene;21-hydroxy-d4-pregnane-3,20-dione;21-hydroxy-d4-pregnene-3,20-dione;21-hydroxy-pregn-4-ene-3,20-dione;21-hydroxy-progesterone;21-hydroxypregn-4-ene-3,20-dione;21-hydroxyprogesterone;4-pregnen-21-ol-3,20-dione;Cortexone;D4-pregnene-21-ol-3,20-dione;Doc;Deoxycortone;Desoxycorticosterone;Desoxycortone;Doca;Kendall's desoxy compound b;Reichstein's substance q;21-hydroxy-4-pregnene-3,20-dione;DeoxycorticosteronePW_C000010Doct2284322994978976112121815407124368119202721-HydroxypregnenoloneHMDB000402621-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575).1164-98-3C0548524702028043216208[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC21H32O3InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1MOIQRAOBRXUWGN-WPWXJNKXSA-N2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one332.477332.23514489-3.87221-hydroxypregnenolone00FDB023281(3b)-3,21-dihydroxy-pregn-5-en-20-one;21-hydroxypregnenolone;3b,21-dihydroxy-5-pregnen-20-one;3b,21-dihydroxy-pregn-5-en-20-one;5-pregnen-3.beta.,21-diol-20-one;5-pregnen-3b,21-diol-20-one;5-pregnen-3beta,21-diol-20-one;Oprea1_642453;Pregn-5-ene-3b,21-diol-20-one;(3beta)-3,21-dihydroxypregn-5-en-20-one;(3b)-3,21-dihydroxypregn-5-en-20-one;(3β)-3,21-dihydroxypregn-5-en-20-onePW_C00202721-Hpgn22884978977331121816383124369398721NADHMDB0000902NAD (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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951144NADHHMDB0001487NADH 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_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951216ProgesteroneHMDB0001830The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. -- Pubchem; Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. -- Wikipedia; During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. -- Wikipedia.57-83-0C00410599417026CPD-2725773DB00396[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O2InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1RJKFOVLPORLFTN-LEKSSAKUSA-N(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one314.4617314.224580204-4.760(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB00187117a-progesterone;3,20-pregnene-4;4-pregnen-3,20-dione;4-pregnene-3,20-dione;Agolutin;Bio-luton;Cidr;Colprosterone;Corlutin;Corlutina;Corluvite;Corporin;Corpus luteum hormone;Crinone;Crinone progesterone gel;Curretab;Cyclogest;Cyclogesterin;D4-pregnene-3,20-dione;Delalutin;Duraprogen;Estima;Flavolutan;Fologenon;Gesterol;Gesterol 100;Gesterol 50;Gestiron;Gestone;Gestormone;Gestron;Glanducorpin;Gynlutin;Gynoluton;Gynolutone;Hormoflaveine;Hormoluton;Hydroxyprogesterone caproate;Hydroxyprogesterone caproic acid;Lingusorbs;Lipo-lutin;Lucorteum;Lucorteum sol;Lugesteron;Luteal hormone;Luteocrin normale;Luteodyn;Luteogan;Luteohormone;Luteol;Luteopur;Luteosan;Luteostab;Luteovis;Luteum;Lutex;Lutidon;Lutociclina;Lutocuclin m;Lutocyclin;Lutocyclin m;Lutocylin;Lutocylol;Lutoform;Lutogyl;Lutren;Lutromone;Mpa;Membrettes;Methylpregnone;Nalutron;Percutacrine;Percutacrine luteinique;Piaponon;Pranone;Pregn-4-en-3,20-dione;Pregn-4-ene-3,20-dione;Pregnene-3,20-dione;Pregnenedione;Primolut;Prochieve;Progeffik;Progekan;Progestan;Progestasert;Progesterol;Progesterone;Progesteronum;Progestin;Progestogel;Progestol;Progeston;Progestone;Progestosol;Progestron;Progestronol;Projestaject;Prolets;Prolidon;Prolutin;Proluton;Prolutone;Prometrium;Prontogest;Protormone;Syngesterone;Syngestrets;Synovex s;Syntolutan;Utrogest;Utrogestan;Vitarrine;Beta-progesterone;Delta(sup 4)-pregnene-3,20-dione;(s)-4-pregnene-3,20-dione;(s)-pregn-4-en-3,20-dione;(s)-progesterone;17alpha-progesterone;Akrolutin;Delta(4)-pregnene-3,20-dione;Gelbkoerperhormon;Progesteron;17α-progesterone;δ(4)-pregnene-3,20-dionePW_C001216Prgstrn228949238318238487897813078997111121820125121840122124373136124393135173PregnenoloneHMDB0000253Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809).145-13-1C019535347767816581PREGNENOLONE[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC21H32O2InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1ORNBQBCIOKFOEO-QGVNFLHTSA-N1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one316.4776316.240230268-4.3711-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone00FDB021920(3b)-3-hydroxy-pregn-5-en-20-one;3-hydroxypregn-5-en-20-one;3b-hydroxypregn-5-en-20-one;3beta-hydroxypregn-5-en-20-one;5-pregnen-3b-ol-20-one;5-pregnen-3beta-ol-20-one;Natolone;Pregn-5-en-3b-ol-20-one;Pregn-5-ene-3b-ol-20-one;Pregnetan;Pregneton;Pregnolon;Prenolon;Regnosone;SkinostelonPW_C000173Pregnen2294497897933112182138312437439827317-HydroxyprogesteroneHMDB0000374It serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase. 17-Hydroxyprogesterone is a natural progestin and in pregnancy increases in the third trimester primarily due to fetal adrenal production. This hormone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase and 11β-hydroxylase, lead to a build-up of 17OHP. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17OHP. 17OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17OHP is also contributed by the placenta.68-96-2C011766238172526002[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O3InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1DBPWSSGDRRHUNT-CEGNMAFCSA-N(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one330.4611330.219494826-4.051(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02199217-hydroxypregn-4-ene-3,20-dione;17-hydroxyprogesterone;17-oh progesterone;17-ohp;17-alpha-hydroxyprogesterone;17a-hydroxypregn-4-ene-3,20-dione;17a-hydroxyprogesterone;17alpha-hydroxyprogesterone;D4-pregnen-17a-ol-3,20-dione;Gestageno;Gestageno gador;Hydroxyprogesterone;Pregn-4-en-17a-ol-3,20-dione;Prodix;Prodox;17-hydroxypregn-4-en-3,20-dione;17alpha-hydroxy-4-pregnene-3,20-dione;17alpha-hydroxy-progesterone;Delta(4)-pregnene-17alpha-ol-3,20-dione;Hidroxiprogesterona;Hydroxyprogesteronum;Pregn-4-ene-3,20-dione-17-ol;17α-hydroxyprogesterone;17a-hydroxy-4-pregnene-3,20-dione;17α-hydroxy-4-pregnene-3,20-dione;17a-hydroxy-progesterone;17α-hydroxy-progesterone;Delta(4)-pregnene-17a-ol-3,20-dione;δ(4)-pregnene-17α-ol-3,20-dione;δ(4)-pregnene-17a-ol-3,20-dionePW_C00027317-OHP313121422102226492308377366331789801121218224071223423831243751191248943981265114951280853909CortexoloneHMDB0000015Cortexolone is the precursor of cortisol. Accumulation of cortexolone can happen in a defect known as congenital adrenal hyperplasia, which is due to 11-beta-hydroxylase deficiency, resulting in androgen excess, virilization, and hypertension (PMID: 2022736). Cortexolone is a 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities (PubChem).152-58-9C054884407072832411-DEOXY-CORTISOL389582[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H30O4InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1WHBHBVVOGNECLV-OBQKJFGGSA-N(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one346.4605346.214409448-4.142(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one00FDB02187211-deoxy-17-hydroxy-corticosterone;11-deoxy-17-hydroxycorticosterone;11-deoxy-cortisol;11-deoxycortisol;11-deoxyhydrocortisone;11-desoxy-17-hydroxycorticosterone;11-desoxycortisol;11-desoxyhydrocortisone;11-dioxy-cortisol;11-dioxycortisol;17,21-dihydroxy-4-pregnene-3,20-dione;17,21-dihydroxypregn-4-ene-3,20-dione;17,21-dihydroxyprogesterone;17-hydroxy-11-deoxycorticosterone;17alpha-hydroxycortexone;20-dione 17,21-dihydroxypregn-4-ene-3;4-pregnene-17alpha,21-diol-3,20-dione;Cortodoxone;Reichstein s;Reichstein's compound s;Reichstein's substance sPW_C000009Cortexo112316231132319157898111212182340712437611926317a-HydroxypregnenoloneHMDB000036317a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809).387-79-1C05138914512875082579[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC21H32O3InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1JERGUCIJOXJXHF-TVWVXWENSA-N1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one332.477332.23514489-3.9521-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone00FDB02198217-hydroxy-d5-pregnenolone;17-hydroxypregnenolone;17-oh-pregnenolone;17a-hydroxypregnolone;17alpha-hydroxypregnanolone;17alpha-hydroxypregnenolone;3b,17-dihydroxy-5-pregnen-20-one;3b,17-dihydroxy-pregn-5-en-20-one;3b,17a-dihydroxypregn-5-en-20-one;5-pregnen-3b,17a-diol-20-one;(3beta)-3,17-dihydroxypregn-5-en-20-one;5-pregnen-3beta,17alpha-diol-20-one;(3b)-3,17-dihydroxypregn-5-en-20-one;(3β)-3,17-dihydroxypregn-5-en-20-one;17a-hydroxypregnenolone;17α-hydroxypregnenolone;5-pregnen-3β,17α-diol-20-onePW_C00026317a-HP307103121214233622284977369331121824383124377398126514495128088390291417α,21-DihydroxypregnenoloneHMDB000676217alpha,21-Dihydroxypregnenolone is an intermediate in the human fetus at midpregnancy that is converted into cortisol (PMID: 4231965). It has also been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions. In normal adrenal slices from patients with hypernephroid kidney carcinomas these pathways bypass cholesterol, pregnenolone, and progesterone, and proceed to 21-hydroxypregnenolone (PMID: 6247575). 17alpha,21-Dihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxypregnenolone is the 5th to last step in the synthesis of Cortol and is converted from 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.99.10). It is then converted to 11beta,17alpha,21-Trihydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.15.4).1167-48-2C0548719273527832167253[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC21H32O4InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1JNHJGXQUDOYJAK-IYRCEVNGSA-N1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one348.4764348.230059512-3.7931-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone00FDB02406517α,21-Dihydroxypregnenolone;17,21-Dihydroxypregnenolone;3β,17α,21-Trihydroxypregnenone;3beta,17alpha,21-Trihydroxypregnenone;3β,17,21-Trihydroxy-pregn-5-en-20-one;3beta,17,21-Trihydroxy-pregn-5-en-20-one;(3β)-3,17,21-Trihydroxypregn-5-en-20-one;(3beta)-3,17,21-Trihydroxypregn-5-en-20-one;3β,17α,21-Trihydroxypregn-5-en-20-one;3beta,17alpha,21-Trihydroxypregn-5-en-20-onePW_C00291417ADhp23174978982331121825383124378398291520a,22b-DihydroxycholesterolHMDB000676320alpha,22beta-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 20alpha,22beta-Dihydroxycholesterol is the 8th to last step in the synthesis of 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.15.6). It is then converted to Pregnenolone via the enzyme cytochrome P450 (EC 1.14.15.6).15234-55-6C05501534778971294[H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12CC27H46O3InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1ISBSSBGEYIBVTO-IVMOZYHGSA-N(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol418.6523418.344695338-4.723(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol00FDB02406620alpha,22beta-dihydroxycholesterol;Not availablePW_C002915OH2chol232137898311212182640712437911910164-MethylpentanalHMDB00013184-Methylpentanal, also known as isocaproaldehyde or isohexanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Methylpentanal is slightly soluble (in water) and an extremely weak acidic (essentially neutral) compound (based on its pKa). Within the cell, 4-methylpentanal is primarily located in the mitochondria and cytoplasm. In humans, 4-methylpentanal is involved in the steroidogenesis pathway. 4-Methylpentanal is also involved in several metabolic disorders, some of which include 3-Beta-hydroxysteroid dehydrogenase deficiency, corticosterone methyl oxidase II deficiency - cmo II, adrenal hyperplasia type 5 or congenital adrenal hyperplasia due to 17 Alpha-hydroxylase deficiency, and the apparent mineralocorticoid excess syndrome pathway. 4-Methylpentanal is an intermediate in the metabolism of C21-Steroid hormone. It is a substrate for Cytochrome P450 11A1 (mitochondrial).1119-16-0C02373129179984-METHYLPENTANAL126CC(C)CCC=OC6H12OInChI=1S/C6H12O/c1-6(2)4-3-5-7/h5-6H,3-4H2,1-2H3JGEGJYXHCFUMJF-UHFFFAOYSA-N4-methylpentanal100.1589100.088815006-1.420isocaproaldehyde00FDB0225514-methyl valeraldehyde;4-methyl-valeraldehyde;4-methylpentanal;4-methylvaleraldehyde;Isocaproaldehyde: 4-methyl-pentanal;Isohexana;Isocaproaldehyde;IsohexanalPW_C0010164-MPnal2322378984112121827407124380119291617a,20a-DihydroxycholesterolHMDB000676417alpha,20alpha-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 17alpha,20alpha-Dihydroxycholesterol is the 8th to last step in the synthesis of Cortolone and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.99.9). It is then converted to 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC1.14.15.6).C05499 53477898783[H]C12CC[C@](O)([C@](C)(O)CCCC(C)C)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC27H46O3InChI=1S/C27H46O3/c1-18(2)7-6-13-26(5,29)27(30)16-12-23-21-9-8-19-17-20(28)10-14-24(19,3)22(21)11-15-25(23,27)4/h8,18,20-23,28-30H,6-7,9-17H2,1-5H3/t20-,21+,22?,23?,24-,25-,26+,27+/m0/s1PRZXKPDANWDCNC-IMVKCWHASA-N(2R,5S,10R,14R,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol418.6523418.344695338-4.893(2R,5S,10R,14R,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol00FDB02406717alpha,20alpha-dihydroxycholesterolPW_C00291617aDhch2326378986112121829407124382119203122b-HydroxycholesterolHMDB000403522b-Hydroxycholesterol, also known as (22R)-OH-cholesterol or cholest-5-en-3b,22R-diol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is considered to be a practically insoluble (in water) and relatively neutral molecule. 22b-Hydroxycholesterol has been found in human epidermis, hepatic and endocrine gland tissues, and has also been primarily detected in urine. Within the cell, 22b-hydroxycholesterol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 22b-hydroxycholesterol is involved in the steroidogenesis pathway. 22b-Hydroxycholesterol is also involved in several metabolic disorders, some of which include corticosterone methyl oxidase I deficiency (cmo I), adrenal hyperplasia type 5 or congenital adrenal hyperplasia due to 17 Alpha-hydroxylase deficiency, 17-alpha-hydroxylase deficiency (cyp17), and 11-beta-hydroxylase deficiency (cyp11b1). 22beta-Hydroxycholesterol is a substrate for DCC-interacting protein 13 beta.17954-98-2C05502167685385115146693[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12CC27H46O2InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1RZPAXNJLEKLXNO-GFKLAVDKSA-N(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol402.6529402.349780716-5.79222R-hydroxycholesterol00FDB023285(3beta,22r)-cholest-5-ene-3,22-diol;22r-hydroxycholesterol;22beta-hydroxycholesterol;Cholest-5-en-3beta,22r-diol;(3b,22r)-cholest-5-ene-3,22-diol;(3β,22r)-cholest-5-ene-3,22-diolPW_C00203122b-HC232937898711212183040712438311947CholesterolHMDB0000067Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50% of the lipid in the membrane or 60-80% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginine (ADMA) in the endothelium since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with highly oxidized levels of LDL, pose a heightened risk factor for vascular disease. Chronically high levels of cholesterol are associated with at least five inborn errors of metabolism, including cerebrotendinous xanthomatosis, cholesteryl ester storage disease, congenital lipoid adrenal hyperplasia, hypercholesterolemia, and Zellweger syndrome. In chronically high levels, cholesterol can function as an atherogen (causes atherosclerosis and cardiovascular disease). Specifically, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease.57-88-5C00187599716113CHOLESTEROL5775DB04540[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1HVYWMOMLDIMFJA-DPAQBDIFSA-N(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol386.6535386.354866094-7.141(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol00FDB013269(+)-ent-cholesterol;(-)-cholesterol;(20bfh)-cholest-5-en-3b-ol;(3b)-cholest-5-en-3-ol;(3beta)-cholest-5-en-3-ol;20-epi-cholesterol;20-iso-cholesterol;20bfh-cholest-5-en-3b-ol;3beta-hydroxycholest-5-ene;5-cholesten-3b-ol;5-cholesten-3beta-ol;5:6-cholesten-3-ol;5:6-cholesten-3beta-ol;Cholest-5-en-3-ol;Cholest-5-en-3b-ol;Cholest-5-en-3beta-ol;Cholesterin;Cholesterine;Cholesterol;Cholesterol base h;Cholesteryl alcohol;Cholestrin;Cholestrol;Cordulan;Dastar;Dusoline;Dusoran;Dythol;Epicholesterin;Epicholesterol;Fancol ch;Hydrocerin;Kathro;Lanol;Liquid crystal cn/9;Nimco cholesterol base h;Nimco cholesterol base no. 712;Super hartolan;TegolanPW_C000047Lanol82921658492330328402928451573412137567210764916077653336776851147895133178988112121516383121697429121731409121831407124074398124246464124282137124384119270420α-HydroxycholesterolHMDB000628320alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol lipid molecule. 20alpha-Hydroxycholesterol is considered to be a practically insoluble (in water) and relatively neutral molecule. 20alpha-Hydroxycholesterol has been found throughout all human tissues, and has also been primarily detected in urine. Within the cell, 20alpha-hydroxycholesterol is primarily located in the membrane (predicted from logP), mitochondria and cytoplasm. In humans, 20alpha-hydroxycholesterol is involved in the steroidogenesis pathway. 20alpha-Hydroxycholesterol is also involved in several metabolic disorders, some of which include corticosterone methyl oxidase II deficiency - cmo II, the apparent mineralocorticoid excess syndrome pathway, corticosterone methyl oxidase I deficiency (cmo I), and the congenital lipoid adrenal hyperplasia (clah) or lipoid cah pathway. 20 alpha-hydroxycholesterol participates in C21-Steroid hormone metabolism. 20 alpha-hydroxycholesterol is produced by the reaction between cholesterol and the enzyme, cholesterol monooxygenase (side-chain-cleaving) [EC:1.14.15.6].516-72-3C05500440711129620A-HYDROXY-CHOLESTEROL389586DB04704CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12CC27H46O2InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1MCKLJFJEQRYRQT-MGNSQDQZSA-N(1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol402.6529402.349780716-5.85220a-hydroxy cholesterol00FDB023876(3beta,20r)-cholest-5-ene-3,20-diol;20-hydroxycholesterol;20alpha-hydroxycholesterol;20alpha-hydroxy cholesterolPW_C00270420a-HC2334378989112121832407124385119291117a,21-Dihydroxy-5b-pregnane-3,11,20-trioneHMDB000675817alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is the second to last step in the synthesis of Cortolone and is converted. from Cortisone via the enzyme Delta4-3-oxosteroid 5beta-reductase (EC 1.3.1.3). It is then converted to Urocortisone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).68-54-2C05469655541809358997[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12CC21H30O5InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-15,18,22,26H,3-11H2,1-2H3/t12-,14+,15+,18-,19+,20+,21+/m1/s1YCLWEYIBFOLMEM-FNLRALKVSA-N(1S,2S,7R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione362.4599362.20932407-3.452dihydrocortisone00FDB02406217,21-dihydroxy-5-beta-pregnane-3,11,20-trione;17,21-dihydroxy-5b-pregnane-3,11,20-trione;17alpha,21-dihydroxy-5beta-pregnane-3,11,20-trione;4,5-b-dihydrocortisone;4,5-beta-dihydrocortisone;4,5beta-dihydrocortisone;5-dihydrocortisone;5beta-pregnane-17alpha,21-diol-3,11,20-trione;17a,21-dihydroxy-5b-pregnane-3,11,20-trione;17α,21-dihydroxy-5β-pregnane-3,11,20-trione;17,21-dihydroxy-5β-pregnane-3,11,20-trione;4,5b-dihydrocortisone;4,5β-dihydrocortisone;5b-pregnane-17a,21-diol-3,11,20-trione;5β-pregnane-17α,21-diol-3,11,20-trionePW_C002911DHPRGT23688789911111218341221243871351708CortisoneHMDB0002802Cortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver into the active metabolite cortisol (Martindale, The Extra Pharmacopoeia, 30th ed, p726). Cortisone is a corticosteroid hormone released by the adrenal gland in response to stress. One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness (Wikipedia).53-06-5C0076222278616962CPD-286193441[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC21H28O5InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1MFYSYFVPBJMHGN-ZPOLXVRWSA-N(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione360.444360.193674006-3.422(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione00FDB023065Andreson;Anusol hc;Balneol-hc;Colocort;Compound e;Corlin;Cortadren;Cortandren;Cortef;Cortef acetate;Cortisal;Cortisate;Cortison;Cortisone acetate;Cortistal;Cortivite;Cortogen;Cortone;Cortril;Dermacort;Dricort;Flexicort;Florinef;Fludrocortisone acetate;Glycort;Hemsol-hc;Hi-cor;Incortin;Kendall's compound e;Kendall's compound;Locoid;Locoid lipocream;Micort-hc;Nogenic hc;Orabase hca;Pandel;Prestwick_132;Reichstein fa;Reichstein's substance fa;Scheroson;Solu-cortef;Stie-cort;Texacort;Westcort;Beta-hc;11-dehydro-17-hydroxycorticosterone;17-hydroxy-11-dehydrocorticosterone;17alpha,21-dihydroxy-4-pregnene-3,11,20-trione;4-pregnene-17alpha,21-diol-3,11,20-trione;Delta(4)-pregnene-17alpha,21-diol-3,11,20-trione;Kortison;Pregn-4-en-17alpha,21-diol-3,11,20-trione;Wintersteiner's compound f;17a,21-dihydroxy-4-pregnene-3,11,20-trione;17α,21-dihydroxy-4-pregnene-3,11,20-trione;4-pregnene-17a,21-diol-3,11,20-trione;4-pregnene-17α,21-diol-3,11,20-trione;Delta(4)-pregnene-17a,21-diol-3,11,20-trione;δ(4)-pregnene-17α,21-diol-3,11,20-trione;Pregn-4-en-17a,21-diol-3,11,20-trione;Pregn-4-en-17α,21-diol-3,11,20-trione;δ(4)-pregnene-17a,21-diol-3,11,20-trionePW_C001708Corlin22774978992331121835383124388398722TetrahydrocortisoneHMDB0000903Cortisol is a corticosteroid hormone that is involved in the response to stress; it increases blood pressure and blood sugar levels and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation. -- Wikipedia; As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. -- Wikipedia.53-05-41244461716735652[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12CC21H32O5InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1SYGWGHVTLUBCEM-SDYDLROXSA-N(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one364.4758364.224974134-3.273(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one00FDB022310(3a,5b)-3,17,21-trihydroxy-pregnane-11,20-dione;3,17-dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one;3a,17,21-trihydroxy-5a-pregnane-11,20-dione;3a,17,21-trihydroxy-5b-pregnane-11,20-dione;3alpha,17,21-trihydroxypregnane-11,20-dione;3alpha,17,21-trihydroxy-5beta-pregnane-11,20-dione;3b,17,21-trihydroxy-5a-pregnane-11,20-dione;5a-pregnan-3b,17a,21-triol-11,20-dion;Ba 2681;Tetrahydro e;Tetrahydro-cortisone;Tetrahydrocompound e;Tetrahydrocortison;Tetrahydrocortisone;UrocortisonePW_C000722TetraHC23698789931111218361221243891351823DihydrocortisolHMDB0003259Dihydrocortisol is the product of the enzyme Steroid 5-beta-reductase [EC 1.3.1.3], which catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone, testosterone, aldosterone, corticosterone and cortisol to 5-beta-reduced metabolites. A deficiency in this enzyme is associated with congenital defect in bile acid synthesis. (OMIM 235555). Dihydrocortisol is the substrate of the enzyme 3-alpha-hydroxysteroid dehydrogenase[EC:1.1.1.225 1.1.1.213 1.3.1.20 1.1.1.50], and is an iintermediate in the Bile acid biosynthesis, C21-Steroid hormone metabolism, Androgen and estrogen metabolism, and in the Metabolism of xenobiotics by cytochrome P450. (KEGG).1482-50-4C05471164838144508[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12CC21H32O5InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1ACSFOIGNUQUIGE-AIPUTVCKSA-N(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one364.4758364.224974134-3.233dihydrocortisol00FDB0231335-beta-dihydrocortisol;5beta-pregnane-11beta,17alpha,21-triol-3,20-dione;5b-pregnane-11b,17a,21-triol-3,20-dione;5β-pregnane-11β,17α,21-triol-3,20-dionePW_C001823DHCort2371878994111121837122124390135757TetrahydrocortisolHMDB0000949Tetrahydrocortisol, also known as dihydrocortison or urocortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Tetrahydrocortisol is considered to be a practically insoluble (in water) and relatively neutral molecule. Tetrahydrocortisol has been found in human hepatic tissue, and has also been primarily detected in urine. Within the cell, tetrahydrocortisol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, tetrahydrocortisol is involved in the steroidogenesis pathway. Tetrahydrocortisol is also involved in several metabolic disorders, some of which include 11-beta-hydroxylase deficiency (cyp11b1), adrenal hyperplasia type 5 or congenital adrenal hyperplasia due to 17 Alpha-hydroxylase deficiency, the apparent mineralocorticoid excess syndrome pathway, and corticosterone methyl oxidase II deficiency - cmo II. Tetrahydrocortisol is the most powerful natural angiostatic steroid. It is involved in C21-Steroid hormone metabolism pathway (KEGG).53-02-1C054724472571721506239C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)COC21H34O5InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12?,13-,14?,15?,16+,18?,19+,20+,21+/m1/s1AODPIQQILQLWGS-OBRSLYEHSA-N2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one366.4917366.240624198-2.9042-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone00FDB0223332-hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone;3a,11b,17,21-tetrahydroxy-5b-pregnan-20-one;3b,11b,17,21-tetrahydroxy-5b-pregnan-20-one;3b,11b,17a,21-tetrahydroxy-5b-pregnan-20-on;5b-tetrahydrocortisol;Dihydrocortison;Tetrahydro-cortisol;Tetrahydrocortisol;UrocortisolPW_C000757tetHCol2372878995111121838122124391135291311b,17a,21-Trihydroxypreg-nenoloneHMDB000676011beta,17alpha,21-Trihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 11beta,17alpha,21-Trihydroxypregnenolone is the 4th to last step in the synthesis of Cortol and is converted from 17alpha,21-Dihydroxypregnenolone via the enzyme cytochrome P450 (EC:1.14.15.4). It is then converted to Cortisol via the enzyme 3beta-hydroxy-delta5-steroid dehydrogenase (EC 1.1.1.145) and the enzyme steroid delta-isomerase (EC 5.3.3.1).C05489440708389583CC12CC(O)C3C(CC=C4CC(O)CCC34C)C1CC[C@]2(O)C(=O)COC21H32O5InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h3,13-16,18,22-24,26H,4-11H2,1-2H3/t13?,14?,15?,16?,18?,19?,20?,21-/m0/s1HAFVWTUQBYRPOB-QGGNSXJXSA-N2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one364.4758364.224974134-2.8342-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethanone00FDB02406411beta,17alpha,21-trihydroxypreg-nenolone;11beta,17alpha,21-trihydroxypregnenolonePW_C002913Trihpnn2382497899633112183938312439239819645a-Pregnane-3,20-dioneHMDB00037595a-Pregnane-3,20-dione, also known as 3,20-allopregnanedione or 5-a-dihydroprogesterone, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 5a-pregnane-3,20-dione is considered to be a steroid lipid molecule. 5a-Pregnane-3,20-dione exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. 5a-Pregnane-3,20-dione has been found in human hepatic and testicle tissues, and has also been detected in multiple biofluids, such as blood and urine. Within the cell, 5a-pregnane-3,20-dione is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 5a-pregnane-3,20-dione is involved in the steroidogenesis pathway. 5a-Pregnane-3,20-dione is also involved in several metabolic disorders, some of which include corticosterone methyl oxidase I deficiency (cmo I), 11-beta-hydroxylase deficiency (cyp11b1), adrenal hyperplasia type 3 or congenital adrenal hyperplasia due to 21-hydroxylase deficiency, and 21-hydroxylase deficiency (cyp21). 5a-Pregnane-3,20-dione is a biologically active 5-alpha-reduced metabolite of plasma progesterone. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (allopregnanolone), a neuroactive steroid that binds with GABA(A) receptor.566-65-4C036819281028952CPD-29383782[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12CC21H32O2InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1XMRPGKVKISIQBV-BJMCWZGWSA-N(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one316.4776316.240230268-5.3905a-pregnane-3,20-dione00FDB0232223,20-allopregnanedione;3,20-dioxo-5a-pregnane;3,20-dioxo-5alpha-pregnane;5-alpha-dihydroprogesterone;5-alpha-pregnane-3,20-dione;5a-dihydroprogesterone;5a-pregnan-3,20-dione;5a-pregnane-3,20-dione;5alpha-dihydroprogesterone;5alpha-pregnane-3,20-dione;5alpha-pregnan-3,20-dione;5b-pregnane-3,20-dione;5beta-pregnane-3,20-dione;Allopregnan-3,20-dione;Pregnane-3,20-dione;5α-pregnane-3,20-dione;3,20-dioxo-5α-pregnane;5-a-dihydroprogesterone;5-α-dihydroprogesterone;5α-dihydroprogesteronePW_C001964P3D238587899811112184112212439413529123a-Hydroxy-5b-pregnane-20-oneHMDB00067593alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).C054802477961423141070[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2C21H34O2InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16?,17-,18?,19?,20+,21-/m1/s1AURFZBICLPNKBZ-KCZNCWLVSA-N1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one318.4935318.255880332-5.371pregnanolone00FDB0240633alpha-hydroxy-5beta-pregnane-20-onePW_C0029123aH5bPO238687899911112184212212439513533Reduced adrenal ferredoxinProteinComplexPW_EC00003316906ChEBIRAF34Oxidized adrenal ferredoxinProteinComplexPW_EC00003416341ChEBIOAF40Reduced acceptorCompoundPW_EC00004015022ChEBIRA41AcceptorCompoundPW_EC00004115339ChEBIAccepto165303-alpha-hydroxysteroid dehydrogenaseQ6LDE7
Besides being a 3-alpha-hydroxysteroid dehydrogenase, the enzyme can accomplish diverse functions: as quinone reductase, as an aromatic alcohol dehydrogenase, as dihydrodiol dehydrogenase, and as 9-, 11-, and 15-hydroxyprostaglandin dehydrogenase.
Akr1c9171.1.1.50124211118124254464124351135165333-oxo-5-beta-steroid 4-dehydrogenaseP31210
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Akr1d1171.3.1.312421346412435313512528011816625Cytochrome P450 11B3, mitochondrialP30100
Converts 11-deoxycorticosterone into corticosterone, 18-hydroxycorticosterone, and aldosterone. Also can catalyze the conversion of 11-deoxycortisol to cortisol, 18-hydroxycortisol and cortisone.
Cyp11b3171.14.15.4; 1.14.15.512435511912527812116628Corticosteroid 11-beta-dehydrogenase isozyme 1Q6LDH6
Catalyzes reversibly the conversion of corticosterone to 11-dehydrocorticosterone.
Hsd11b1171.1.1.14612436239816633Steroid 21-hydroxylaseQ64562
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Cyp21171.14.14.1612436439816636Steroid 17-alpha-hydroxylase/17,20 lyaseQ6LAE5
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Cyp17a1171.14.14.19; 1.14.14.32124366398124386119166403 beta-hydroxysteroid dehydrogenase type 5A0A0G2JSR3Hsd3b51712437239816642Cholesterol side-chain cleavage enzyme, mitochondrialQ6LDR9
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone, the precursor of most steroid hormones.
Cyp11a1171.14.15.612438111916644Corticosteroid 11-beta-dehydrogenase isozyme 2P50233
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Hsd11b2171.1.1.-1243961361243973989193Aldo-keto reductase family 1 member C417PW_P009193174491653091943-oxo-5-beta-steroid 4-dehydrogenase17PW_P009194174501653319222Cytochrome P450 11B217PW_P009222174781662519223Cytochrome P450 11B117PW_P009223174791662519224Corticosteroid 11-beta-dehydrogenase isozyme 117PW_P009224174801662829225Steroid 21-hydroxylase17PW_P009225174811663319226Steroid 17-alpha-hydroxylase/17,20 lyase17PW_P0092261748216636192273-beta-HSD 117PW_P009227174831664019228Cholesterol side-chain cleavage enzyme, mitochondrial17PW_P009228174841664219229Corticosteroid 11-beta-dehydrogenase isozyme 217PW_P0092291748516644192303 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 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2053 C1738 2474 1738 3266 1738 3672 91false60.01619.0368536M2144 2055 C2144 2511 2145 3257 2145 3669 91false61.01614.0368537M2537 2060 C2537 2589 2535 3097 2535 3668 91false62.01608.0368538M48 668 C48 618 98 568 148 568 C1417 568 3067 568 4336 568 C4386 568 4436 618 4436 668 C4436 1784 4436 3236 4436 4352 C4436 4402 4386 4452 4336 4452 C3067 4452 1417 4452 148 4452 C98 4452 48 4402 48 4352 C48 3236 48 1784 48 668 1true64388.03884.0368539M3019 2542 C3019 2492 3069 2442 3119 2442 C3381 2442 3721 2442 3983 2442 C4033 2442 4083 2492 4083 2542 C4083 2664 4083 2823 4083 2945 C4083 2995 4033 3045 3983 3045 C3721 3045 3381 3045 3119 3045 C3069 3045 3019 2995 3019 2945 C3019 2823 3019 2664 3019 2542 84true61064.0603.0368540M2895 2425 C2895 2375 2945 2325 2995 2325 C3323 2325 3750 2325 4078 2325 C4128 2325 4178 2375 4178 2425 C4178 2613 4178 2859 4178 3047 C4178 3097 4128 3147 4078 3147 C3750 3147 3323 3147 2995 3147 C2945 3147 2895 3097 2895 3047 C2895 2859 2895 2613 2895 2425 84true61283.0822.044732915Adrenal Gland725130201.01.01601544733015Smooth Endoplasmic Reticulum22751495201.01.01601544733115Smooth Endoplasmic Reticulum2352505201.01.01601544733215ER Membrane16552055201.01.01601544733315ER Membrane20602055201.01.01601544733415ER Membrane24502055201.01.01601544733515Mitochondrion11802310201.01.01601544733615Mitochondrion11903115201.01.01601544733715Mitochondrion24053850201.01.01601544733815Mitochondrion34251980201.01.01601544733915Intracellular Space115605201.01.01601544734015Extracellular Space110305201.01.01601544734115Inner mitochondria membrane29752450201.01.01601544734215Outer mitochondria membrane28302385201.01.0160151798992393177215472041276736854#FFEEDE4122016441799003700209928212281423031844#FFEBEB41409903179901419270056923911108352939#FFEEDE4539113817990282332285214483448844447539673-beta-Hydroxysteroid Dehydrogenase Deficiency3-beta (β)-hydroxysteroid dehydrogenase (HSD) deficiency is an inherited disorder that affects hormone-producing glands including the gonads (ovaries in females and testes in males) and the adrenal glands.Mutations in the HSD3B2 gene cause 3β-HSD deficiency. The HSD3B2 gene provides instructions for making the 3β-HSD enzyme. This enzyme is found in the gonads and adrenal glands. The 3β-HSD enzyme is involved in the production of many hormones, including cortisol, aldosterone, androgens, and estrogen. Cortisol has numerous functions such as maintaining energy and blood sugar levels, protecting the body from stress, and suppressing inflammation.DiseasePW_X009337CompleteContext93375065216640ProteinMutated5065345CompoundDecreased5065412TissueDamaged506551TissueDamaged2780087626445Simard J, Rheaume E, Mebarki F, Sanchez R, New MI, Morel Y, Labrie F: Molecular basis of human 3 beta-hydroxysteroid dehydrogenase deficiency. J Steroid Biochem Mol Biol. 1995 Jun;53(1-6):127-38.9337Context279317Simard J, Ricketts M, Gingras S, Soucy P, Feltus FA, Melner MH: Molecular Biology of the 3β-Hydroxysteroid Dehydrogenase/Δ5-Δ4 Isomerase Gene Family. Endocrine Reviews. 2005 Jun 01;26(4):525-582. doi: 10.1210/er.2002-0050.9337Context