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CHEBI:17347 ChEBI 1.0 1.0 Transport1572 false 11b-Hydroxyandrost-4-ene-3,17-dione (→) Transport: Homo sapiens, Cell, Mitochondrial Inner Membrane to Homo sapiens, Cell, Endoplasmic Reticulum Membrane LEFT_TO_RIGHT 937 ChemSpider C00674 KEGG Compound 439153 PubChem-compound 1.0 ReactionCatalysis946 ACTIVATION 3-oxo-5-beta-steroid 4-dehydrogenase ReactionCatalysis62992 ACTIVATION 6013 PubChem-compound ReactionCatalysis62991 ACTIVATION ReactionCatalysis62994 ACTIVATION ReactionCatalysis62993 ACTIVATION ReactionCatalysis62996 ACTIVATION Oxidized flavoprotein ReactionCatalysis62995 ACTIVATION ReactionCatalysis62998 ACTIVATION ReactionCatalysis62997 ACTIVATION 3-oxo-5-alpha-steroid 4-dehydrogenase 1 102793 ChemSpider NADPH C19H28O2 Androstanedione 288.20892 53-41-8 CAS 1.0 HMDB0006768 HMDB 19-Hydroxyandrost-4-ene-3,17-dione Cytochrome P450 19A1 NADH CHEBI:17200 ChEBI 1.0 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider HMDB0006773 HMDB 2.0 HMDB0006772 HMDB C00468 KEGG Compound UDP-GLUCURONATE BioCyc 6031 PubChem-compound 1.0 Q6IN67 UniProt 1010 ChemSpider 1.0 1.0 HMDB0004484 HMDB 1.0 Q9HCN8 UniProt Cytochrome P450 11B1, mitochondrial Testosterone C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 1.0 1.0 CHEBI:17263 ChEBI Cytosol C19H24O3 Adrenosterone 300.17255 1.0 1.0 CHEBI:5086 ChEBI C19H26O3 11b-Hydroxyandrost-4-ene-3,17-dione 302.1882 C25H38O8 Androsterone glucuronide 466.25668 84958 ChemSpider UDP-glucuronosyltransferase 1-1 1.0 Etiocholanedione ANDROSTERONE BioCyc C00007 KEGG Compound C00006 KEGG Compound CHEBI:18009 ChEBI Hydrogen Ion C00001 KEGG Compound Beta-D-Glucuronides BioCyc P18405 UniProt C00005 KEGG Compound C00004 KEGG Compound C19H28O2 Etiocholanedione 288.20892 C00003 KEGG Compound NADPH Androsterone glucuronide Mitochondrial Inner Membrane 1.0 Oxygen C11135 KEGG Compound NADH C11136 KEGG Compound C21H28N7O14P2 NAD 664.11694 5669 ChemSpider 5668 ChemSpider 6128 PubChem-compound 78 kDa glucose-regulated protein HMDB0000902 HMDB CHEBI:16032 ChEBI C00015 KEGG Compound Oxygen 5660 ChemSpider NAD(P) BioCyc P37058 UniProt H Hydrogen Ion 1.007825 C19H24O3 19-Oxoandrost-4-ene-3,17-dione 300.17255 194597 ChemSpider 5898 ChemSpider Androstenedione 53-84-9 CAS Protein disulfide-isomerase A2 C03772 KEGG Compound ALPHA-ANDROSTAN-3BETA17BETA-DIOL BioCyc 94141 PubChem-compound HYOU1 protein NADP 1.14.14.14 false 1.14.14.14 19-Oxoandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → Estrone + Formic acid + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 19-Hydroxyandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → 19-Oxoandrost-4-ene-3,17-dione + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT 1.0 1.14.14.14 false 1.14.14.14 Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Oxidized flavoprotein + Water LEFT_TO_RIGHT SMILES NC(=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]1O 17465008 ChemSpider 3-oxo-5-alpha-steroid 4-dehydrogenase 1 HMDB0003769 HMDB C00280 KEGG Compound CHEBI:607862 ChEBI HMDB0000490 HMDB P17516 UniProt C00167 KEGG Compound HMDB0000145 HMDB Cytochrome P450 11B1, mitochondrial Testosterone 17-beta-dehydrogenase 3 C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 CHEBI:28195 ChEBI Etiocholanolone HMDB0000142 HMDB Oxidized adrenal ferredoxin C05297 KEGG Compound 19-Hydroxyandrost-4-ene-3,17-dione 1.0 7732-18-5 CAS C00058 KEGG Compound 1.0 1.0 HMDB0001487 HMDB Water SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Androstanedione SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Corticosteroid 11-beta-dehydrogenase isozyme 1 FORMATE BioCyc HMDB0000031 HMDB 3602-09-3 CAS 16522 ChemSpider NAD Corticosteroid 11-beta-dehydrogenase isozyme 1 1.0 2.0 1.0 HMDB0001377 HMDB Androstenedione Metabolism 1.0 1.0 962 PubChem-compound 58-98-0 CAS Reduced adrenal ferredoxin Oxidized adrenal ferredoxin 1.0 2.0 Reduced flavoprotein Oxidized flavoprotein C00080 KEGG Compound 1.0 SMILES O=O 114833 PubChem-compound Hydrogen Ion P28845 UniProt HMDB0000053 HMDB HMDB0000295 HMDB HMDB0002111 HMDB SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 5809 ChemSpider SMILES OC=O 1.0 443078 PubChem-compound P15538 UniProt 64-18-6 CAS 3-oxo-5-beta-steroid 4-dehydrogenase 16399653 PubChem-compound 19-Oxoandrost-4-ene-3,17-dione 22833512 PubChem-compound SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO 1.0 H2O Water 18.010565 SMP0030406 SMPDB Uridine 5'-diphosphate NADH BioCyc 2.0 NAD BioCyc 1.0 53-42-9 CAS 977 PubChem-compound HMDB0059597 HMDB Testosterone 17-beta-dehydrogenase 3 Q15084 UniProt P23284 UniProt Androstenedione P51857 UniProt SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O 1.0 17215925 ChemSpider P13667 UniProt HMDB0002829 HMDB 11b-Hydroxyandrost-4-ene-3,17-dione HMDB0000899 HMDB SMILES O C19H28O2 Testosterone 288.20892 Stromal cell-derived factor 2-like protein 1 Cytochrome P450 19A1 1.0 2616-64-0 CAS C19H26O2 Androstenedione 286.19327 1.0 Reduced flavoprotein C04373 KEGG Compound Uridine diphosphate glucuronic acid CHEBI:15846 ChEBI 382-44-5 CAS 5870 PubChem-compound 53-59-8 CAS Adrenosterone 1038 PubChem-compound ReactionCatalysis34 ACTIVATION ReactionCatalysis35 ACTIVATION Endoplasmic reticulum resident protein 29 ReactionCatalysis33 ACTIVATION GO:0005829 GENE ONTOLOGY 278 ChemSpider 5879 PubChem-compound Etiocholanolone glucuronide P11021 UniProt 1.0 CHEBI:16906 ChEBI C19H30O2 Etiocholanolone 290.22458 CHEBI:16908 ChEBI 1.0 1.0 221136 ChemSpider SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O HMDB0003955 HMDB C21H30N7O17P3 NADPH 745.0911 Hydrogen Ion C21H29N7O17P3 NADP 744.08325 C19H30O2 Androsterone 290.22458 1.0 NADPH BioCyc 1.0 CPD-6641 BioCyc ANDROST4ENE BioCyc 58-68-4 CAS SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C HMDB0000217 HMDB C19H26O3 19-Hydroxyandrost-4-ene-3,17-dione 302.1882 NAD Q96GW1 UniProt 1.0 510-64-5 CAS Oxygen CHEBI:16985 ChEBI Androstenedione Q13087 UniProt 1852-43-3 CAS CPD-342 BioCyc Q9UBS4 UniProt 1.0 58-22-0 CAS SMILES NC(=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]1O HMDB0000221 HMDB SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C Protein disulfide-isomerase A6 CHEBI:28832 ChEBI C25H38O8 Etiocholanolone glucuronide 466.25668 SMILES NC(=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]1O 17473 PubChem-compound 53-57-6 CAS DnaJ homolog subfamily B member 11 Protein disulfide-isomerase A4 1.0 HSP90B1 protein 1.0 HMDB0000234 HMDB C21H29N7O14P2 NADH 665.12476 GO:0005743 GENE ONTOLOGY 1.0 UDP-glucuronosyltransferase 1-1 CHEBI:15994 ChEBI Stromal cell-derived factor 2-like protein 1 Endoplasmic reticulum resident protein 29 Protein disulfide-isomerase A4 Protein disulfide-isomerase A6 Peptidyl-prolyl cis-trans isomerase B 1.0 Water HYOU1 protein Protein disulfide-isomerase A2 Reduced adrenal ferredoxin 78 kDa glucose-regulated protein Androsterone C05285 KEGG Compound C05284 KEGG Compound CHEBI:27967 ChEBI 1.0 Androstanedione DnaJ homolog subfamily B member 11 Endoplasmic Reticulum Endoplasmic Reticulum Membrane SMILES NC(=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]1O Androstenedione 5682 ChemSpider UDP BioCyc 223997 PubChem-compound Corticosteroid 11-beta-dehydrogenase isozyme 1 1.0 Reduced flavoprotein Aldo-keto reductase family 1 member C4 C05290 KEGG Compound P30040 UniProt P22309 UniProt CHEBI:16422 ChEBI 193520 ChemSpider SMILES [H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O 5675 ChemSpider HMDB0000935 HMDB 5791 ChemSpider 846-46-8 CAS 1229-12-5 CAS Water 18971002 PubChem-compound 391377 ChemSpider CHEBI:37451 ChEBI 1.0 Homo sapiens ESTRONE BioCyc 388299 ChemSpider 1.0 C18H22O2 Estrone 270.162 HSP90B1 protein O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 GO:0005789 GENE ONTOLOGY GO:0005783 GENE ONTOLOGY SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C 7782-44-7 CAS 9606 TAXONOMY 53-16-7 CAS 1.0 UDP-glucuronosyltransferase 1-1 222865 PubChem-compound 5893 PubChem-compound 1.0 1.1.1.50 false 1.1.1.50 Androstanedione + Hydrogen Ion + NADH → Androsterone + NAD LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT 1.0 PW031290 PathWhiz CHEBI:30751 ChEBI Etiocholanolone Oxidized flavoprotein Reaction72862 false Androstenedione + 2 Hydrogen Ion + Oxygen + 2 Reduced adrenal ferredoxin → 11b-Hydroxyandrost-4-ene-3,17-dione + 2 Oxidized adrenal ferredoxin + Water LEFT_TO_RIGHT Reaction72863 false 11b-Hydroxyandrost-4-ene-3,17-dione + NADP → Adrenosterone + Hydrogen Ion + NADPH LEFT_TO_RIGHT Reaction72864 false Androstenedione + Hydrogen Ion + NADPH → Etiocholanedione + NADP LEFT_TO_RIGHT 1.1.1.50 false 1.1.1.50 Etiocholanedione + Hydrogen Ion + NADH → Etiocholanolone + NAD LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Reaction72867 false Androstenedione + Hydrogen Ion + NADPH → Androstanedione + NADP LEFT_TO_RIGHT Cytochrome P450 19A1 CHEBI:15377 ChEBI 5880 PubChem-compound CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] C00523 KEGG Compound 1.0 5886 PubChem-compound CHEBI:16341 ChEBI Aldo-keto reductase family 1 member C4 1.0 11b-Hydroxyandrost-4-ene-3,17-dione Peptidyl-prolyl cis-trans isomerase B 2.0 C00535 KEGG Compound 1.0 1.0 SMILES [H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C 1.0 Estrone SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O SMILES O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C CHEBI:27576 ChEBI 63-05-8 CAS NADP CHEBI:17659 ChEBI P11511 UniProt 1.1.1.64 false 1.1.1.64 NAD + Testosterone ↔ Androstenedione + Hydrogen Ion + NADH REVERSIBLE CHEBI:1069535 ChEBI 1.0 Formic acid 389114 ChemSpider SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C 440114 PubChem-compound 1.0 252379 PubChem-compound 382-45-6 CAS Androsterone 3-oxo-5- alpha-steroid 4-dehydrogenase 1 Aldo-keto reductase family 1 member C4 UDP- glucuronosyltransferase 1-1 Cytochrome P450 19A1 Cytochrome P450 19A1 Cytochrome P450 19A1 Testosterone 17-beta- dehydrogenase 3 Cytochrome P450 11B1, mitochondrial 3-oxo-5-beta- steroid 4-dehydrogenase UDP- glucuronosyltransferase 1-1 Corticosteroid 11-beta- dehydrogenase isozyme 1 Aldo-keto reductase family 1 member C4 11b- Hydroxyandrost- 4-ene-3,17- dione 11b- Hydroxyandrost- 4-ene-3,17- dione Androstenedione NADPH H + Androstanedione NADP NADH H + Androsterone NAD Uridine diphosphate glucuronic acid Androsterone glucuronide Uridine 5'-diphosphate O 2 19- Hydroxyandrost- 4-ene-3,17- dione H 2 O O 2 19- Oxoandrost-4- ene-3,17- dione H 2 O O 2 Estrone Formic acid H 2 O Testosterone NAD NADH H + O 2 H + H 2 O NADPH H + NADP Etiocholanedione Etiocholanolone Uridine diphosphate glucuronic acid Etiocholanolone glucuronide Uridine 5'-diphosphate NADP NADPH H + Adrenosterone NADH H + NAD Heme Reduced flavoprotein Oxidized flavoprotein Reduced flavoprotein Oxidized flavoprotein Reduced flavoprotein Oxidized flavoprotein Reduced adrenal ferredoxin Oxidized adrenal ferredoxin Heme Heme Heme Mitochondrial Inner Membrane Mitochondrial Outer Membrane Mitochondrial Matrix Mitochondrial Intermembrane Space Endoplasmic Reticulum Membrane Cytosol
CHEBI:17347 ChEBI 1.0 1.0 Transport1572 false 11b-Hydroxyandrost-4-ene-3,17-dione (→) Transport: Homo sapiens, Cell, Mitochondrial Inner Membrane to Homo sapiens, Cell, Endoplasmic Reticulum Membrane LEFT_TO_RIGHT 937 ChemSpider C00674 KEGG Compound 439153 PubChem-compound 1.0 ReactionCatalysis946 ACTIVATION 3-oxo-5-beta-steroid 4-dehydrogenase ReactionCatalysis62992 ACTIVATION 6013 PubChem-compound ReactionCatalysis62991 ACTIVATION ReactionCatalysis62994 ACTIVATION ReactionCatalysis62993 ACTIVATION ReactionCatalysis62996 ACTIVATION Oxidized flavoprotein ReactionCatalysis62995 ACTIVATION ReactionCatalysis62998 ACTIVATION ReactionCatalysis62997 ACTIVATION 3-oxo-5-alpha-steroid 4-dehydrogenase 1 102793 ChemSpider NADPH C19H28O2 Androstanedione 288.20892 53-41-8 CAS 1.0 HMDB0006768 HMDB 19-Hydroxyandrost-4-ene-3,17-dione Cytochrome P450 19A1 NADH CHEBI:17200 ChEBI 1.0 CHEBI:16474 ChEBI Hydrogen Ion 952 ChemSpider HMDB0006773 HMDB 2.0 HMDB0006772 HMDB C00468 KEGG Compound UDP-GLUCURONATE BioCyc 6031 PubChem-compound 1.0 Q6IN67 UniProt 1010 ChemSpider 1.0 1.0 HMDB0004484 HMDB 1.0 Q9HCN8 UniProt Cytochrome P450 11B1, mitochondrial Testosterone C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 1.0 1.0 CHEBI:17263 ChEBI Cytosol C19H24O3 Adrenosterone 300.17255 1.0 1.0 CHEBI:5086 ChEBI C19H26O3 11b-Hydroxyandrost-4-ene-3,17-dione 302.1882 C25H38O8 Androsterone glucuronide 466.25668 84958 ChemSpider UDP-glucuronosyltransferase 1-1 1.0 Etiocholanedione ANDROSTERONE BioCyc C00007 KEGG Compound C00006 KEGG Compound CHEBI:18009 ChEBI Hydrogen Ion C00001 KEGG Compound Beta-D-Glucuronides BioCyc P18405 UniProt C00005 KEGG Compound C00004 KEGG Compound C19H28O2 Etiocholanedione 288.20892 C00003 KEGG Compound NADPH Androsterone glucuronide Mitochondrial Inner Membrane 1.0 Oxygen C11135 KEGG Compound NADH C11136 KEGG Compound C21H28N7O14P2 NAD 664.11694 5669 ChemSpider 5668 ChemSpider 6128 PubChem-compound 78 kDa glucose-regulated protein HMDB0000902 HMDB CHEBI:16032 ChEBI C00015 KEGG Compound Oxygen 5660 ChemSpider NAD(P) BioCyc P37058 UniProt H Hydrogen Ion 1.007825 C19H24O3 19-Oxoandrost-4-ene-3,17-dione 300.17255 194597 ChemSpider 5898 ChemSpider Androstenedione 53-84-9 CAS Protein disulfide-isomerase A2 C03772 KEGG Compound ALPHA-ANDROSTAN-3BETA17BETA-DIOL BioCyc 94141 PubChem-compound HYOU1 protein NADP 1.14.14.14 false 1.14.14.14 19-Oxoandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → Estrone + Formic acid + Oxidized flavoprotein + Water LEFT_TO_RIGHT 1.14.14.14 false 1.14.14.14 19-Hydroxyandrost-4-ene-3,17-dione + Oxygen + Reduced flavoprotein → 19-Oxoandrost-4-ene-3,17-dione + Oxidized flavoprotein + 2 Water LEFT_TO_RIGHT 1.0 1.14.14.14 false 1.14.14.14 Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Oxidized flavoprotein + Water LEFT_TO_RIGHT SMILES NC(=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]1O 17465008 ChemSpider 3-oxo-5-alpha-steroid 4-dehydrogenase 1 HMDB0003769 HMDB C00280 KEGG Compound CHEBI:607862 ChEBI HMDB0000490 HMDB P17516 UniProt C00167 KEGG Compound HMDB0000145 HMDB Cytochrome P450 11B1, mitochondrial Testosterone 17-beta-dehydrogenase 3 C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 CHEBI:28195 ChEBI Etiocholanolone HMDB0000142 HMDB Oxidized adrenal ferredoxin C05297 KEGG Compound 19-Hydroxyandrost-4-ene-3,17-dione 1.0 7732-18-5 CAS C00058 KEGG Compound 1.0 1.0 HMDB0001487 HMDB Water SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Androstanedione SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C Corticosteroid 11-beta-dehydrogenase isozyme 1 FORMATE BioCyc HMDB0000031 HMDB 3602-09-3 CAS 16522 ChemSpider NAD Corticosteroid 11-beta-dehydrogenase isozyme 1 1.0 2.0 1.0 HMDB0001377 HMDB Androstenedione Metabolism 1.0 1.0 962 PubChem-compound 58-98-0 CAS Reduced adrenal ferredoxin Oxidized adrenal ferredoxin 1.0 2.0 Reduced flavoprotein Oxidized flavoprotein C00080 KEGG Compound 1.0 SMILES O=O 114833 PubChem-compound Hydrogen Ion P28845 UniProt HMDB0000053 HMDB HMDB0000295 HMDB HMDB0002111 HMDB SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 5809 ChemSpider SMILES OC=O 1.0 443078 PubChem-compound P15538 UniProt 64-18-6 CAS 3-oxo-5-beta-steroid 4-dehydrogenase 16399653 PubChem-compound 19-Oxoandrost-4-ene-3,17-dione 22833512 PubChem-compound SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO 1.0 H2O Water 18.010565 SMP0030406 SMPDB Uridine 5'-diphosphate NADH BioCyc 2.0 NAD BioCyc 1.0 53-42-9 CAS 977 PubChem-compound HMDB0059597 HMDB Testosterone 17-beta-dehydrogenase 3 Q15084 UniProt P23284 UniProt Androstenedione P51857 UniProt SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O 1.0 17215925 ChemSpider P13667 UniProt HMDB0002829 HMDB 11b-Hydroxyandrost-4-ene-3,17-dione HMDB0000899 HMDB SMILES O C19H28O2 Testosterone 288.20892 Stromal cell-derived factor 2-like protein 1 Cytochrome P450 19A1 1.0 2616-64-0 CAS C19H26O2 Androstenedione 286.19327 1.0 Reduced flavoprotein C04373 KEGG Compound Uridine diphosphate glucuronic acid CHEBI:15846 ChEBI 382-44-5 CAS 5870 PubChem-compound 53-59-8 CAS Adrenosterone 1038 PubChem-compound ReactionCatalysis34 ACTIVATION ReactionCatalysis35 ACTIVATION Endoplasmic reticulum resident protein 29 ReactionCatalysis33 ACTIVATION GO:0005829 GENE ONTOLOGY 278 ChemSpider 5879 PubChem-compound Etiocholanolone glucuronide P11021 UniProt 1.0 CHEBI:16906 ChEBI C19H30O2 Etiocholanolone 290.22458 CHEBI:16908 ChEBI 1.0 1.0 221136 ChemSpider SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O HMDB0003955 HMDB C21H30N7O17P3 NADPH 745.0911 Hydrogen Ion C21H29N7O17P3 NADP 744.08325 C19H30O2 Androsterone 290.22458 1.0 NADPH BioCyc 1.0 CPD-6641 BioCyc ANDROST4ENE BioCyc 58-68-4 CAS SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C HMDB0000217 HMDB C19H26O3 19-Hydroxyandrost-4-ene-3,17-dione 302.1882 NAD Q96GW1 UniProt 1.0 510-64-5 CAS Oxygen CHEBI:16985 ChEBI Androstenedione Q13087 UniProt 1852-43-3 CAS CPD-342 BioCyc Q9UBS4 UniProt 1.0 58-22-0 CAS SMILES NC(=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]1O HMDB0000221 HMDB SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C Protein disulfide-isomerase A6 CHEBI:28832 ChEBI C25H38O8 Etiocholanolone glucuronide 466.25668 SMILES NC(=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]1O 17473 PubChem-compound 53-57-6 CAS DnaJ homolog subfamily B member 11 Protein disulfide-isomerase A4 1.0 HSP90B1 protein 1.0 HMDB0000234 HMDB C21H29N7O14P2 NADH 665.12476 GO:0005743 GENE ONTOLOGY 1.0 UDP-glucuronosyltransferase 1-1 CHEBI:15994 ChEBI Stromal cell-derived factor 2-like protein 1 Endoplasmic reticulum resident protein 29 Protein disulfide-isomerase A4 Protein disulfide-isomerase A6 Peptidyl-prolyl cis-trans isomerase B 1.0 Water HYOU1 protein Protein disulfide-isomerase A2 Reduced adrenal ferredoxin 78 kDa glucose-regulated protein Androsterone C05285 KEGG Compound C05284 KEGG Compound CHEBI:27967 ChEBI 1.0 Androstanedione DnaJ homolog subfamily B member 11 Endoplasmic Reticulum Endoplasmic Reticulum Membrane SMILES NC(=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]1O Androstenedione 5682 ChemSpider UDP BioCyc 223997 PubChem-compound Corticosteroid 11-beta-dehydrogenase isozyme 1 1.0 Reduced flavoprotein Aldo-keto reductase family 1 member C4 C05290 KEGG Compound P30040 UniProt P22309 UniProt CHEBI:16422 ChEBI 193520 ChemSpider SMILES [H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O 5675 ChemSpider HMDB0000935 HMDB 5791 ChemSpider 846-46-8 CAS 1229-12-5 CAS Water 18971002 PubChem-compound 391377 ChemSpider CHEBI:37451 ChEBI 1.0 Homo sapiens ESTRONE BioCyc 388299 ChemSpider 1.0 C18H22O2 Estrone 270.162 HSP90B1 protein O2 Oxygen 31.98983 CH2O2 Formic acid 46.005478 GO:0005789 GENE ONTOLOGY GO:0005783 GENE ONTOLOGY SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C 7782-44-7 CAS 9606 TAXONOMY 53-16-7 CAS 1.0 UDP-glucuronosyltransferase 1-1 222865 PubChem-compound 5893 PubChem-compound 1.0 1.1.1.50 false 1.1.1.50 Androstanedione + Hydrogen Ion + NADH → Androsterone + NAD LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT 1.0 PW031290 PathWhiz CHEBI:30751 ChEBI Etiocholanolone Oxidized flavoprotein Reaction72862 false Androstenedione + 2 Hydrogen Ion + Oxygen + 2 Reduced adrenal ferredoxin → 11b-Hydroxyandrost-4-ene-3,17-dione + 2 Oxidized adrenal ferredoxin + Water LEFT_TO_RIGHT Reaction72863 false 11b-Hydroxyandrost-4-ene-3,17-dione + NADP → Adrenosterone + Hydrogen Ion + NADPH LEFT_TO_RIGHT Reaction72864 false Androstenedione + Hydrogen Ion + NADPH → Etiocholanedione + NADP LEFT_TO_RIGHT 1.1.1.50 false 1.1.1.50 Etiocholanedione + Hydrogen Ion + NADH → Etiocholanolone + NAD LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Reaction72867 false Androstenedione + Hydrogen Ion + NADPH → Androstanedione + NADP LEFT_TO_RIGHT Cytochrome P450 19A1 CHEBI:15377 ChEBI 5880 PubChem-compound CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] C00523 KEGG Compound 1.0 5886 PubChem-compound CHEBI:16341 ChEBI Aldo-keto reductase family 1 member C4 1.0 11b-Hydroxyandrost-4-ene-3,17-dione Peptidyl-prolyl cis-trans isomerase B 2.0 C00535 KEGG Compound 1.0 1.0 SMILES [H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C 1.0 Estrone SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O SMILES O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C CHEBI:27576 ChEBI 63-05-8 CAS NADP CHEBI:17659 ChEBI P11511 UniProt 1.1.1.64 false 1.1.1.64 NAD + Testosterone ↔ Androstenedione + Hydrogen Ion + NADH REVERSIBLE CHEBI:1069535 ChEBI 1.0 Formic acid 389114 ChemSpider SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C 440114 PubChem-compound 1.0 252379 PubChem-compound 382-45-6 CAS Androsterone