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MetaCyc Compound: 4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol

Superclasses: a lipidan isoprenoida terpenoida triterpenoid
a secondary metabolitea terpenoida triterpenoid
a steroida hydroxysteroida sterol

Citations: [Benveniste02]

Chemical Formula: C30H50O2

Molecular Weight: 442.72 Daltons

Monoisotopic Molecular Weight: 442.3810808492 Daltons

4α-hydroxymethyl-stigmasta-7,24(24<sup>1</sup>)-dien-3β-ol compound structure

SMILES: CC=C(C(C)C)CCC(C)[CH]3(CC[CH]4(C2(=CC[CH]1(C(CO)C(O)CCC(C)1[CH]2CCC(C)34))))

InChI: InChI=1S/C30H50O2/c1-7-21(19(2)3)9-8-20(4)24-12-13-25-22-10-11-26-23(18-31)28(32)15-17-30(26,6)27(22)14-16-29(24,25)5/h7,10,19-20,23-28,31-32H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24-,25+,26+,27+,28+,29-,30+/m1/s1


Unification Links: PubChem:50986085

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 514.13605Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

plant sterol biosynthesis :
4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NADH + oxygen + H+ → 4α-formyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + 2 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:

plant sterol biosynthesis :
24-ethylidenelophenol + NADH + oxygen + H+4α-hydroxymethyl-stigmasta-7,24(241)-dien-3β-ol + NAD+ + 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 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+

Created 10-Dec-2010 by Dreher KA, TAIR


Benveniste02: Benveniste, P. (2002). "Sterol Metabolism." : March 27, 2002. The Arabidopsis Book. Rockville, MD: American Society of Plant Biologists. doi: 10.1199/tab.0004, http://www.aspb.org/publications/arabidopsis/.

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 Tue Jan 1, 2002, biocyc12.