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MetaCyc Compound: 5β-cholestane-3α,7α,12α-triol

Superclasses: a steroida hydroxysteroida 17-alpha-hydroxysteroid
a steroida hydroxysteroida sterola 3alpha-hydroxysteroid

Chemical Formula: C27H48O3

Molecular Weight: 420.67 Daltons

Monoisotopic Molecular Weight: 420.3603454071 Daltons

5β-cholestane-3α,7α,12α-triol compound structure

SMILES: CC(C)CCCC(C)[CH]1(CC[CH]2(C(C)1C(O)C[CH]3([CH]2C(O)C[CH]4(C(C)3CCC(O)C4))))

InChI: InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChIKey: InChIKey=RIVQQZVHIVNQFH-XJZYBRFWSA-N

Unification Links: ChEBI:16496, ChemSpider:141053, HMDB:HMDB01457, KEGG:C05454, LIPID MAPS:LMST04030035, MetaboLights:MTBLC16496, PubChem:160520

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 409.5238Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

bile acid biosynthesis, neutral pathway :
5β-cholestane-3α,7α,12α-triol + 2 a reduced adrenodoxin + 2 H+ + oxygen → (25R)-5β-cholestane-3α,7α,12α,26-tetraol + 2 an oxidized adrenodoxin + H2O

Not in pathways:
5β-cholestane-3α,7α,12α-triol + 6 a reduced adrenodoxin + 5 H+ + 3 oxygen → (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oate + 6 an oxidized adrenodoxin + 4 H2O

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

Reactions known to produce the compound:

bile acid biosynthesis, neutral pathway :
5β-cholestane-3α,7α,12α-triol + NAD(P)+ ← 7α,12α-dihydroxy-5β-cholestan-3-one + NAD(P)H + H+

Not in pathways:
5β-cholestane-3α,7α-diol + NAD(P)H + oxygen + H+5β-cholestane-3α,7α,12α-triol + NAD(P)+ + H2O

sphingolipid biosynthesis (plants) :
a dihydroceramide + a sterol 3-β-D-glucoside → a D-glucosyl-N-acylsphinganine + a sterol

Not in pathways:
a steryl-ester + H2O → a fatty acid + a sterol + H+

In Reactions of unknown directionality:

Not in pathways:
a 3α-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+

Not in pathways:
a sterol + a phosphatidylcholine = a 1-acyl 2-lyso-phosphatidylcholine + a steryl-ester
a sterol + a 1,2-diacyl-sn-glycerol = 1-acyl-sn-glycerol + a steryl-ester
UDP-α-D-glucose + a sterol = UDP + a sterol 3-β-D-glucoside + H+

Credits:
Revised 12-Nov-2012 by Caspi R, 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."


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 Fri Apr 29, 2016, biocyc14.