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

Default Structure
ChEBI IDCHEBI:66459
ChEBI Name3,4-secoisopimara-4(18),7,15-triene-3-oic acid
Stars
DefinitionA diterpenoid of the class of secoisopimarane isolated from Salvia cinnabarina and has been shown to exhibit antispasmodic, hypotensive and antibacterial activities.
Last Modified2 July 2013
DownloadsMolfile
FormulaC20H30O2
Net Charge0
Average Mass302.458
Monoisotopic Mass302.22458
SMILES[H][C@]12CC[C@](C)(C=C)CC1=CC[C@@H](C(=C)C)[C@]2(C)CCC(=O)O
InChIInChI=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
InChIKeyXQZUWQQUDZZOHA-ZULIPRJHSA-N
Species of MetaboliteComponentSourceComments
Salvia cinnabarina (ncbitaxon:933125) leaf (BTO:0000713) PubMed (11301863)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Application:
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 Relation(s)
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 NumbersSources
Reaxys:22892163Reaxys
Citations