petasin (CHEBI:8030)

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ChEBI Name	petasin

ChEBI ID	CHEBI:8030

Definition	An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-ol.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C20H28O3

Net Charge

Average Mass

316.43450

Monoisotopic Mass

316.20384

InChI

InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1

InChIKey

ISTBXSFGFOYLTM-NZEDGPFZSA-N

SMILES

C\C=C(\C)C(=O)O[C@@H]1CCC2=CC(=O)[C@@H](C[C@]2(C)[C@H]1C)C(C)=C

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator Any compound that binds to and activates the enzyme [hydroxymethylglutaryl-CoA reductase (NADPH)] kinase (EC 2.7.11.31).

Application(s):	vasodilator agent A drug used to cause dilation of the blood vessels. anti-allergic agent A drug used to treat allergic reactions.

ChEBI Ontology
Outgoing	petasin (CHEBI:8030) has functional parent angelic acid (CHEBI:36431) petasin (CHEBI:8030) has role anti-allergic agent (CHEBI:50857) petasin (CHEBI:8030) has role EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator (CHEBI:85053) petasin (CHEBI:8030) has role plant metabolite (CHEBI:76924) petasin (CHEBI:8030) has role vasodilator agent (CHEBI:35620) petasin (CHEBI:8030) is a alicyclic ketone (CHEBI:36132) petasin (CHEBI:8030) is a enoate ester (CHEBI:51702) petasin (CHEBI:8030) is a enone (CHEBI:51689) petasin (CHEBI:8030) is a sesquiterpenoid (CHEBI:26658)

IUPAC Name

(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

Synonym	Source
(+)-Petasin	ChemIDplus

Last Modified

02 March 2015