MetaCyc Compound: capsaicin

Superclasses: a secondary metabolitean alkaloid

Chemical Formula: C18H27NO3

Molecular Weight: 305.42 Daltons

Monoisotopic Molecular Weight: 305.19909373819996 Daltons

capsaicin compound structure


InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+


Unification Links: ChEBI:3374, ChemSpider:1265957, DrugBank:DB05318, HMDB:HMDB02227, KEGG:C06866, MetaboLights:MTBLC3374, PubChem:1548943

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 243.89026Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

capsaicin biosynthesis :
vanillylamine + 8-methyl-6-nonenoate → capsaicin + H2O

Enzymes inhibited by capsaicin, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: NADH:ubiquinone oxidoreductase (H+-transporting) [Satoh96, Yagi90]


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

Satoh96: Satoh T, Miyoshi H, Sakamoto K, Iwamura H (1996). "Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases." Biochim Biophys Acta 1273(1);21-30. PMID: 8573592

Yagi90: Yagi T (1990). "Inhibition by capsaicin of NADH-quinone oxidoreductases is correlated with the presence of energy-coupling site 1 in various organisms." Arch Biochem Biophys 281(2);305-11. PMID: 2118334

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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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