superpathway of cholesterol degradation I (cholesterol oxidase)
Thomas ST, VanderVen BC, Sherman DR, Russell DG, Sampson NS. Pathway profiling in Mycobacterium tuberculosis: elucidation of cholesterol-derived catabolite and enzymes that catalyze its metabolism. J Biol Chem. 2011 Dec 23;286(51):43668–78. PMID: 22045806; PMCID: PMC3243565.; van der Geize R, Grommen AWF, Hessels GI, Jacobs AAC, Dijkhuizen L. The Steroid Catabolic Pathway of the Intracellular Pathogen Rhodococcus equi Is Important for Pathogenesis and a Target for Vaccine Development. PLoS Pathog. 2011 Aug 25;7(8):e1002181. doi: 10.1371/journal.ppat.1002181.; Kreit J, Sampson NS. Cholesterol oxidase: physiological functions. The FEBS Journal. 2009 Nov 16;276(23):6844–56. doi: 10.1111/j.1742-4658.2009.07378.x.; Petrusma M, Dijkhuizen L, van der Geize R. Rhodococcus rhodochrous DSM 43269 3-ketosteroid 9alpha-hydroxylase, a two-component iron-sulfur-containing monooxygenase with subtle steroid substrate specificity. Appl Environ Microbiol. 2009 Aug;75(16):5300–7. PMID: 19561185; PMCID: PMC2725467.; Horinouchi M, Hayashi T, Koshino H, Kurita T, Kudo T. Identification of 9,17-Dioxo-1,2,3,4,10,19-Hexanorandrostan-5-oic Acid, 4-Hydroxy-2-Oxohexanoic Acid, and 2-Hydroxyhexa-2,4-Dienoic Acid and Related Enzymes Involved in Testosterone Degradation in Comamonas testosteroni TA441. Appl Environ Microbiol. 2005 Sep;71(9):5275–81. doi: 10.1128/aem.71.9.5275-5281.2005.; Richmond W. Preparation and Properties of a Cholesterol Oxidase from Nocardia sp. and Its Application to the Enzymatic Assay of Total Cholesterol in Serum. 1973 Dec 01;19(12):1350–6. doi: 10.1093/clinchem/19.12.1350.; Stadtman TC, Cherkes A, Anfinsen CB. STUDIES ON THE MICROBIOLOGICAL DEGRADATION OF CHOLESTEROL. Journal of Biological Chemistry. 1954 Feb;206(2):511–23. doi: 10.1016/s0021-9258(19)50819-5.
Metabolites
3-Hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione
Formula: C19H24O3 (300.1725354)
CAS ID: 2394-69-6
3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione
Formula: C19H24O4 (316.1674504)
CAS ID: 2168-61-8
Enzyme
| EC Number | name | full name | note |
|---|---|---|---|
| 1.1.3.6 | cholesterol oxidase | cholesterol:oxygen oxidoreductase | |
| 1.13.11.25 | 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione 4,5-dioxygenase | 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione:oxygen 4,5-oxidoreductase (decyclizing) | |
| 1.14.14.12 | 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione monooxygenase | 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione,FMNH2:oxygen oxidoreductase | |
| 1.14.15.30 | 3-ketosteroid 9alpha-monooxygenase | androsta-1,4-diene-3,17-dione,[reduced ferredoxin]:oxygen oxidoreductase (9alpha-hydroxylating) | |
| 1.2.1.10 | acetaldehyde dehydrogenase (acetylating) | acetaldehyde:NAD+ oxidoreductase (CoA-acetylating) | |
| 3.7.1.17 | 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase ( (2Z,4Z)-2-hydroxyhexa-2,4-dienoate-forming) | |
| 4.1.3.39 | 4-hydroxy-2-oxovalerate aldolase | 4-hydroxy-2-oxopentanoate pyruvate-lyase (acetaldehyde-forming) | |
| 5.3.3.1 | steroid DELTA-isomerase | 3-oxosteroid DELTA5-DELTA4-isomerase | |
| 6.2.1.41 | 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate-CoA ligase | 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate:CoA ligase (AMP-forming) | |
| 6.2.1.42 | 3-oxocholest-4-en-26-oate-CoA ligase | 3-oxocholest-4-en-26-oate:CoA ligase (AMP-forming) |
Proteins
| Protein ID | name | full name |
|---|---|---|
| B6V6V5 | kshA | 3-ketosteroid-9-alpha-monooxygenase, oxygenase component |
| E3UUE6 | fadD19 | 3-oxocholest-4-en-26-oate--CoA ligase |
| P22637 | choB | Cholesterol oxidase |
| Q0S7V5 | fadD3 | 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl:CoA ligase |
| Q0S811 | hsaA | Flavin-dependent monooxygenase, oxygenase subunit HsaA |
| Q0S815 | hsaF | 4-hydroxy-2-oxovalerate aldolase 3 |
| Q0S816 | hsaG | Acetaldehyde dehydrogenase 3 |
| Q9KWQ5 | hsaC | Iron-dependent extradiol dioxygenase |
| Q9KWQ6 | hsaD | 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase |