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MetaCyc Compound: lanosterol

Synonyms: 4,4,14α-trimethyl-5α-cholesta-8,24-dien-3β-ol

Superclasses: a steroid a 14alpha-methylsteroid
a steroid a hydroxysteroid a sterol a 3beta-hydroxysteroid

Summary:
Lanosterol is a tetracyclic triterpenoid, which is the compound from which all steroids are derived.

Chemical Formula: C30H50O

Molecular Weight: 426.72 Daltons

Monoisotopic Molecular Weight: 426.3861662271 Daltons

lanosterol compound structure

SMILES: CC(C)=CCCC(C)[CH]3(CCC4(C)(C2(CC[CH]1(C(C)(C)C(O)CCC(C)1C=2CCC(C)34))))

InChI: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

InChIKey: InChIKey=CAHGCLMLTWQZNJ-BQNIITSRSA-N

Unification Links: CAS:79-63-0 , ChEBI:16521 , DrugBank:DB03696 , HMDB:HMDB01251 , KEGG:C01724 , MetaboLights:MTBLC16521 , PubChem:25200754

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 512.84705 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

cholesterol biosynthesis I , cholesterol biosynthesis III (via desmosterol) :
lanosterol + NADPH + H+ + oxygen → 14-hydroxylanosterol + NADP+ + H2O

cholesterol biosynthesis II (via 24,25-dihydrolanosterol) :
lanosterol + NADPH + H+ → 24,25-dihydrolanosterol + NADP+

sterol:steryl ester interconversion (yeast) :
lanosterol + oleoyl-CoA → lanosteryl oleate + coenzyme A

zymosterol biosynthesis :
lanosterol + 3 NADPH + 3 oxygen + 2 H+ → 14-demethyllanosterol + formate + 3 NADP+ + 4 H2O

Not in pathways:
a 14α-methylsteroid + 3 NADPH + 3 oxygen + 2 H+ → a Δ14steroid + formate + 3 NADP+ + 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:

sterol:steryl ester interconversion (yeast) :
lanosteryl oleate + H2O → lanosterol + oleate + H+

sphingolipid biosynthesis (plants) :
a dihydroceramide + an O-glucosylsterol → 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:

lanosterol biosynthesis :
(3S)-2,3-epoxy-2,3-dihydrosqualene = lanosterol

Not in pathways:
a 3β-hydroxysteroid + a triacyl-sn-glycerol = a 3-β-hydroxysteroid ester + a 1,2-diacyl-sn-glycerol
a 3β-hydroxysteroid + NADP+ = a 3-oxosteroid + NADPH + 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 + an O-glucosylsterol + H+


References

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 SRI International Pathway Tools version 19.0 on Wed Apr 1, 2015, biocyc14.