CHEBI:8030 - petasin

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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 0
Average Mass 316.43450
Monoisotopic Mass 316.204
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
An effector 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.
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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
Manual Xrefs Databases
C00003169 KNApSAcK
C09706 KEGG COMPOUND
Petasin Wikipedia
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Registry Numbers Types Sources
2419978 Reaxys Registry Number Reaxys
26577-85-5 CAS Registry Number KEGG COMPOUND
26577-85-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11105573 PubMed citation Europe PMC
11286996 PubMed citation Europe PMC
17253240 PubMed citation Europe PMC
19719750 PubMed citation Europe PMC
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25550551 PubMed citation Europe PMC
Last Modified
02 March 2015