Metabolism of steroids
Brown MS, Goldstein JL. Cholesterol feedback: from Schoenheimer's bottle to Scap's MELADL. Journal of Lipid Research. 2009 Apr;50():S15–27. doi: 10.1194/jlr.r800054-jlr200.; Dusso AS, Brown AJ, Slatopolsky E. Vitamin D. American Journal of Physiology-Renal Physiology. 2005 Jul;289(1):F8–F28. doi: 10.1152/ajprenal.00336.2004.; Payne AH, Hales DB. Overview of steroidogenic enzymes in the pathway from cholesterol to active steroid hormones. Endocr Rev. 2004 Dec;25(6):947–70. doi: 10.1210/er.2003-0030. PMID: 15583024.; Russell DW. The enzymes, regulation, and genetics of bile acid synthesis. Annu Rev Biochem. 2003;72():137–74. doi: 10.1146/annurev.biochem.72.121801.161712. PMID: 12543708.; Russell DW. Cholesterol biosynthesis and metabolism. Cardiovasc Drugs Ther. 1992 Apr;6(2):103–10. doi: 10.1007/bf00054556. PMID: 1390320.
Metabolites
(24S)-Cholest-5-ene-3beta,7alpha,24-triol
Formula: C27H46O3 (418.34467659999996)
CAS ID: 245523-67-5
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al
Formula: C27H46O4 (434.3395916)
CAS ID: 3836-01-9
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane
Formula: C27H48O3 (420.36032579999994)
CAS ID: 547-96-6
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate
Formula: C27H46O5 (450.3345066)
CAS ID: 547-98-8
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane
Formula: C27H48O4 (436.3552408)
CAS ID: 862-53-3
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
Formula: C29H46O (410.3548466)
CAS ID: 64284-64-6
7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one
Formula: C27H46O3 (418.34467659999996)
CAS ID: 547-97-7
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol
Formula: C29H48O (412.37049579999996)
CAS ID: 19456-83-8
7alpha,12alpha,26-Trihydroxy-5beta-cholestan-3-one
Formula: C27H46O4 (434.3395916)
CAS ID: 78094-12-9
Enzyme
| EC Number | name | full name | note |
|---|---|---|---|
| 1.1.1.- | |||
| 1.1.1.122 | D-threo-aldose 1-dehydrogenase | D-threo-aldose:NAD+ 1-oxidoreductase | |
| 1.1.1.145 | 3beta-hydroxy-DELTA5-steroid dehydrogenase | 3beta-hydroxy-DELTA5-steroid:NAD+ 3-oxidoreductase | |
| 1.1.1.170 | 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating) | 3beta-hydroxysteroid-4alpha-carboxylate:NAD(P)+ 3-oxidoreductase (decarboxylating) | |
| 1.1.1.181 | cholest-5-ene-3beta,7alpha-diol 3beta-dehydrogenase | cholest-5-ene-3beta,7alpha-diol:NAD+ 3-oxidoreductase | |
| 1.1.1.21 | aldose reductase | alditol:NAD(P)+ 1-oxidoreductase | |
| 1.1.1.210 | 3beta(or 20alpha)-hydroxysteroid dehydrogenase | 3beta(or 20alpha)-hydroxysteroid:NADP+ oxidoreductase | |
| 1.1.1.239 | 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+) | 3alpha(or 17beta)-hydroxysteroid:NAD+ oxidoreductase | |
| 1.1.1.270 | 3beta-hydroxysteroid 3-dehydrogenase | 3beta-hydroxysteroid:NADP+ 3-oxidoreductase | |
| 1.1.1.300 | NADP-retinol dehydrogenase | retinol:NADP+ oxidoreductase | |
| 1.1.1.34 | hydroxymethylglutaryl-CoA reductase (NADPH) | (R)-mevalonate:NADP+ oxidoreductase (CoA-acylating) | |
| 1.1.1.372 | D/L-glyceraldehyde reductase | glycerol:NADP+ oxidoreductase (D/L-glyceraldehyde-forming) | |
| 1.1.1.54 | allyl-alcohol dehydrogenase | allyl-alcohol:NADP+ oxidoreductase | |
| 1.1.1.62 | 17beta-estradiol 17-dehydrogenase | 17beta-estradiol:NAD(P)+ 17-oxidoreductase | |
| 1.14.14.14 | aromatase | testosterone monooxygenase (17beta-estradiol-forming) | |
| 1.14.14.154 | sterol 14alpha-demethylase | sterol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (14-methyl cleaving) | |
| 1.14.14.16 | steroid 21-monooxygenase | steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (21-hydroxylating) | |
| 1.14.14.17 | squalene monooxygenase | squalene,NADPH-hemoprotein:oxygen oxidoreductase (2,3-epoxidizing | |
| 1.14.14.19 | steroid 17alpha-monooxygenase | steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating) | |
| 1.14.14.32 | 17alpha-hydroxyprogesterone deacetylase | 17alpha-hydroxyprogesterone,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating, acetate-releasing) | |
| 1.14.15.15 | cholestanetriol 26-monooxygenase | 5beta-cholestane-3alpha,7alpha,12alpha-triol,adrenodoxin:oxygen oxidoreductase (26-hydroxylating) | |
| 1.14.15.16 | vitamin D3 24-hydroxylase | calcitriol,adrenodoxin:oxygen oxidoreductase (24-hydroxylating) | |
| 1.14.15.18 | calcidiol 1-monooxygenase | calcidiol,adrenodoxin:oxygen oxidoreductase (1-hydroxylating) | |
| 1.14.15.4 | steroid 11beta-monooxygenase | steroid,reduced-adrenal-ferredoxin:oxygen oxidoreductase (11beta-hydroxylating) | |
| 1.14.15.6 | cholesterol monooxygenase (side-chain-cleaving) | cholesterol,reduced-adrenal-ferredoxin:oxygen oxidoreductase (side-chain-cleaving) | |
| 1.14.18.9 | 4alpha-methylsterol monooxygenase | 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,ferrocytochrome-b5:oxygen oxidoreductase (C4alpha-methyl-hydroxylating) | |
| 1.14.19.20 | DELTA7-sterol 5(6)-desaturase | DELTA7-sterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating | |
| 1.14.99.38 | cholesterol 25-monooxygenase | cholesterol,hydrogen-donor:oxygen oxidoreductase (25-hydroxylating) | |
| 1.17.99.3 | 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA 24-hydroxylase | (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA:acceptor 24-oxidoreductase (24R-hydroxylating) | |
| 1.18.1.6 | adrenodoxin-NADP+ reductase | adrenodoxin:NADP+ oxidoreductase | |
| 1.3.1.21 | 7-dehydrocholesterol reductase | cholesterol:NADP+ DELTA7-oxidoreductase | |
| 1.3.1.22 | 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) | 3-oxo-5alpha-steroid:NADP+ DELTA4-oxidoreductase | |
| 1.3.1.3 | DELTA4-3-oxosteroid 5beta-reductase | 5beta-cholestan-3-one:NADP+ 4,5-oxidoreductase | |
| 1.3.1.70 | DELTA14-sterol reductase | 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol:NADP+ DELTA14-oxidoreductase | |
| 1.3.1.72 | DELTA24-sterol reductase | sterol:NADP+ DELTA24-oxidoreductase | |
| 1.3.1.94 | polyprenal reductase | dolichal:NADP+ 2,3-oxidoreductase | |
| 2.3.1.155 | acetyl-CoA C-myristoyltransferase | myristoyl-CoA:acetyl-CoA C-myristoyltransferase | |
| 2.3.1.16 | acetyl-CoA C-acyltransferase | acyl-CoA:acetyl-CoA C-acyltransferase | |
| 2.3.1.176 | propanoyl-CoA C-acyltransferase | 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl-CoA:propanoyl-CoA C-acyltransferase | |
| 2.3.1.65 | bile acid-CoA:amino acid N-acyltransferase | choloyl-CoA:glycine N-choloyltransferase | |
| 2.3.1.9 | acetyl-CoA C-acetyltransferase | acetyl-CoA:acetyl-CoA C-acetyltransferase | |
| 2.3.3.10 | hydroxymethylglutaryl-CoA synthase | acetyl-CoA:acetoacetyl-CoA C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming) | |
| 2.5.1.1 | dimethylallyltranstransferase | prenyl-diphosphate:3-methylbut-3-en-1-yl-diphosphate prenyltranstransferase | |
| 2.5.1.10 | (2E,6E)-farnesyl diphosphate synthase | geranyl-diphosphate:isopentenyl-diphosphate geranyltranstransferase | |
| 2.5.1.21 | squalene synthase | (2E,6E)-farnesyl-diphosphate:(2E,6E)-farnesyl-diphosphate farnesyltransferase | |
| 2.5.1.29 | geranylgeranyl diphosphate synthase | (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase | |
| 2.7.1.36 | mevalonate kinase | ATP:(R)-mevalonate 5-phosphotransferase | |
| 3.1.2.1 | acetyl-CoA hydrolase | acetyl-CoA hydrolase | |
| 3.1.2.11 | acetoacetyl-CoA hydrolase | acetoacetyl-CoA hydrolase | |
| 3.1.2.2 | palmitoyl-CoA hydrolase | palmitoyl-CoA hydrolase | |
| 3.1.2.27 | choloyl-CoA hydrolase | choloyl-CoA hydrolase | |
| 3.1.2.3 | succinyl-CoA hydrolase | succinyl-CoA hydrolase | |
| 3.1.2.5 | hydroxymethylglutaryl-CoA hydrolase | (S)-3-hydroxy-3-methylglutaryl-CoA hydrolase | |
| 3.1.6.2 | steryl-sulfatase | steryl-sulfate sulfohydrolase | |
| 3.3.2.11 | cholesterol-5,6-oxide hydrolase | 5,6alpha-epoxy-5alpha-cholestan-3beta-ol hydrolase | |
| 3.4.21.112 | site-1 protease | ||
| 3.4.22.34 | Legumain | ||
| 3.6.1.68 | geranyl diphosphate phosphohydrolase | geranyl-diphosphate phosphohydrolase | |
| 4.1.1.33 | diphosphomevalonate decarboxylase | ATP:(R)-5-diphosphomevalonate carboxy-lyase (adding ATP; isopentenyl-diphosphate-forming) | |
| 4.2.1.107 | 3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-enoyl-CoA hydratase | (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestanoyl-CoA hydro-lyase [(24E)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-enoyl-CoA-forming] | |
| 4.2.1.119 | enoyl-CoA hydratase 2 | (3R)-3-hydroxyacyl-CoA hydro-lyase | |
| 5.1.99.4 | alpha-methylacyl-CoA racemase | 2-Methylacyl-CoA 2-epimerase | |
| 5.3.3.1 | steroid DELTA-isomerase | 3-oxosteroid DELTA5-DELTA4-isomerase | |
| 5.3.3.5 | cholestenol DELTA-isomerase | DELTA7-Cholestenol DELTA7-DELTA8-isomerase | |
| 5.4.99.7 | Lanosterol synthase | (S)-2,3-Epoxysqualene mutase (cyclizing, lanosterol-forming) | |
| 6.2.1.15 | arachidonate-CoA ligase | arachidonate:CoA ligase (AMP-forming) | |
| 6.2.1.24 | phytanate-CoA ligase | phytanate:CoA ligase (AMP-forming) | |
| 6.2.1.3 | long-chain-fatty-acid-CoA ligase | long-chain fatty acid:CoA ligase (AMP-forming) | |
| 6.2.1.7 | cholate-CoA ligase | cholate:CoA ligase (AMP-forming) | |
| 7.6.2.2 | ABC-type xenobiotic transporter | ATP phosphohydrolase (ABC-type, xenobiotic-exporting) | |
| 7.6.2.3 | ABC-type glutathione-S-conjugate transporter | ATP + H2O + glutathione-S-conjugate[side 1] = ADP + phosphate + glutathione-S-conjugate[side 2] |
Proteins
| Protein ID | name | full name |
|---|