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 Change 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,

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."

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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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