3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459)

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ChEBI Name	3,4-secoisopimara-4(18),7,15-triene-3-oic acid

ChEBI ID	CHEBI:66459

Definition	A diterpenoid of the class of secoisopimarane isolated from Salvia cinnabarina and has been shown to exhibit antispasmodic, hypotensive and antibacterial activities.

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

Supplier Information

Download	Molfile XML SDF

Formula

C20H30O2

Net Charge

Average Mass

302.45100

Monoisotopic Mass

302.22458

InChI

InChI=1S/C20H30O2/c1-6-19(4)11-9-17-15(13-19)7-8-16(14(2)3)20(17,5)12-10-18(21)22/h6-7,16-17H,1-2,8-13H2,3-5H3,(H,21,22)/t16-,17-,19-,20-/m0/s1

InChIKey

XQZUWQQUDZZOHA-ZULIPRJHSA-N

SMILES

[H][C@]12CC[C@@](C)(CC1=CC[C@@H](C(C)=C)[C@]2(C)CCC(O)=O)C=C

Metabolite of Species	Details
Salvia cinnabarina (NCBI:txid933125)	Found in leaf (BTO:0000713). See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	antispasmodic drug A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.

ChEBI Ontology
Outgoing	3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) has role antibacterial agent (CHEBI:33282) 3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) has role antispasmodic drug (CHEBI:53784) 3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) has role metabolite (CHEBI:25212) 3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) is a carbobicyclic compound (CHEBI:36785) 3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) is a diterpenoid (CHEBI:23849) 3,4-secoisopimara-4(18),7,15-triene-3-oic acid (CHEBI:66459) is a monocarboxylic acid (CHEBI:25384)

IUPAC Name

3-[(1S,2S,6S,8aS)-6-ethenyl-1,6-dimethyl-2-(prop-1-en-2-yl)-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]propanoic acid

Registry Number	Type	Source
22892163	Reaxys Registry Number	Reaxys

Last Modified

02 July 2013