MetaCyc Compound: 3,7,12-trihydroxycoprostanate

Synonyms: 3,7,12-trihydroxycoprostanic acid, 5-thca, (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholestane-5-carboxylic acid, 3alpha,7alpha,12alpha-trihydroxycoprostanic acid

Superclasses: a steroid

Chemical Formula: C28H47O5

Molecular Weight: 463.68 Daltons

Monoisotopic Molecular Weight: 464.3501746513 Daltons

3,7,12-trihydroxycoprostanate compound structure

SMILES: CC(C)CCCC(C)[CH]4(CC[CH]2(C(C)(C(C[CH]1(C3(C)(CCC(CC(C(=O)[O-])(CC([CH]12)O)3)O)))O)4))

InChI: InChI=1S/C28H48O5/c1-16(2)7-6-8-17(3)19-9-10-20-24-21(13-23(31)27(19,20)5)26(4)12-11-18(29)14-28(26,25(32)33)15-22(24)30/h16-24,29-31H,6-15H2,1-5H3,(H,32,33)/p-1/t17-,18-,19-,20+,21+,22-,23+,24+,26-,27-,28+/m1/s1


Unification Links: ChemSpider:108961, HMDB:HMDB02163, PubChem:122166

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 309.35062Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
a steroid + 2 a reduced adrenodoxin + oxygen + 2 H+ → an 11-β-hydroxysteroid + 2 an oxidized adrenodoxin + H2O

Enzymes inhibited by 3,7,12-trihydroxycoprostanate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: (25R)-3α,7α,12α-trihydroxy-5β-cholestanoyl-CoA ligase [Falany02]


Chiang08: Chiang YR, Ismail W, Heintz D, Schaeffer C, Van Dorsselaer A, Fuchs G (2008). "Study of anoxic and oxic cholesterol metabolism by Sterolibacterium denitrificans." J Bacteriol 190(3);905-14. PMID: 18039763

Falany02: Falany CN, Xie X, Wheeler JB, Wang J, Smith M, He D, Barnes S (2002). "Molecular cloning and expression of rat liver bile acid CoA ligase." J Lipid Res 43(12);2062-71. PMID: 12454267

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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