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MetaCyc Compound: 3-dehydrocholate

Synonyms: 3-dehydrocholic acid

Superclasses: a steroida bile acid

Citations: [Ridlon06]

Chemical Formula: C24H37O5

Molecular Weight: 405.55 Daltons

Monoisotopic Molecular Weight: 406.2719243303 Daltons

3-dehydrocholate compound structure

SMILES: CC(CCC(=O)[O-])[CH]2(CC[CH]3([CH]4(C(O)C[CH]1(CC(=O)CCC(C)1[CH](CC(O)C(C)23)4))))

InChI: InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/p-1/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChIKey: InChIKey=OEKUSRBIIZNLHZ-DJDNIQJZSA-M

Unification Links: PubChem:46926187

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 220.28937Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glycocholate metabolism (bacteria) :
3-dehydrocholate + NADH + H+ → isocholate + NAD+

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

Reactions known to both consume and produce the compound:

glycocholate metabolism (bacteria) :
cholate + NAD+3-dehydrocholate + NADH + H+

Credits:
Created 02-Jun-2010 by Fulcher CA, SRI International


References

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

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

Ridlon06: Ridlon JM, Kang DJ, Hylemon PB (2006). "Bile salt biotransformations by human intestinal bacteria." J Lipid Res 47(2);241-59. PMID: 16299351


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc14.