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MetaCyc Compound: ergosterol 3-O-β-D-glucoside

Synonyms: O-glucosyl-ergosterol

Superclasses: a steroida hydroxysteroida sterola sterol 3-beta-D-glucoside

Chemical Formula: C34H54O6

Molecular Weight: 558.8 Daltons

Monoisotopic Molecular Weight: 558.392039466 Daltons

ergosterol 3-O-β-D-glucoside compound structure

SMILES: CC(C)C(C)C=CC(C)[CH]4(CC[CH]5(C3(=CC=C2(CC(OC1(OC(CO)C(O)C(O)C(O)1))CCC(C)2[CH]3CCC(C)45))))

InChI: InChI=1S/C34H54O6/c1-19(2)20(3)7-8-21(4)25-11-12-26-24-10-9-22-17-23(13-15-33(22,5)27(24)14-16-34(25,26)6)39-32-31(38)30(37)29(36)28(18-35)40-32/h7-10,19-21,23,25-32,35-38H,11-18H2,1-6H3/b8-7+/t20-,21+,23-,25+,26-,27-,28+,29+,30-,31+,32-,33-,34+/m0/s1

InChIKey: InChIKey=MKZPNGBJJJZJMI-VNWFYEGESA-N

Unification Links: PubChem:44237256

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 443.35052Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

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

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:

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

In Reactions of unknown directionality:

Not in pathways:
UDP-α-D-glucose + ergosterol = ergosterol 3-O-β-D-glucoside + UDP + H+

Not in pathways:
UDP-α-D-glucose + a sterol = UDP + a sterol 3-β-D-glucoside + 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:
Created 06-Aug-2009 by Kothari A, 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, biocyc13.