MetaCyc Compound: stigmasterol

Superclasses: a lipidan isoprenoida terpenoida triterpenoid
a secondary metabolitea terpenoida triterpenoid

Citations: [Holmberg02, Schaeffer01]

Chemical Formula: C29H48O

Molecular Weight: 412.7 Daltons

Monoisotopic Molecular Weight: 412.3705161629 Daltons

stigmasterol compound structure

SMILES: CCC(C(C)C)C=CC(C)[CH]3(CC[CH]4([CH]2(CC=C1(CC(O)CCC(C)1[CH]2CCC(C)34))))

InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1


Unification Links: ChEBI:28824, HMDB:HMDB00937, KEGG:C05442, PubChem:5280794

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 522.4438Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

plant sterol biosynthesis :
sitosterol + NADPH + H+ + oxygen → stigmasterol + NADP+ + 2 H2O

In Reactions of unknown directionality:

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


Holmberg02: Holmberg N, Harker M, Gibbard CL, Wallace AD, Clayton JC, Rawlins S, Hellyer A, Safford R (2002). "Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed." Plant Physiol 130(1);303-11. PMID: 12226510

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

Schaeffer01: Schaeffer A, Bronner R, Benveniste P, Schaller H (2001). "The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1." Plant J 25(6);605-15. PMID: 11319028

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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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