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CHEBI:65462 - ballotenic acid

Default Structure
ChEBI IDCHEBI:65462
ChEBI Nameballotenic acid
Stars
DefinitionA diterpenoid that is 3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid substituted by methyl groups at positions 5, 6 and 8a and a 2-(2-oxotetrahydrofuran-3-yl)ethyl group at position 5 (the 4aR,5S,6R,8aR stereoisomer). It is isolated from the whole plant of Ballota limbata (Syn.Otostegia limbata) and acts as a lipoxygenase inhibitor.
Last Modified7 September 2017
DownloadsMolfile
FormulaC20H30O4
Net Charge0
Average Mass334.456
Monoisotopic Mass334.21441
SMILES[H]C1(CC[C@@]2(C)[C@H](C)CC[C@@]3(C)C(C(=O)O)=CCC[C@@]32[H])CCOC1=O
InChIInChI=1S/C20H30O4/c1-13-7-10-20(3)15(17(21)22)5-4-6-16(20)19(13,2)11-8-14-9-12-24-18(14)23/h5,13-14,16H,4,6-12H2,1-3H3,(H,21,22)/t13-,14?,16-,19+,20+/m1/s1
InChIKeyKLTOIXCFCZRIFD-BBOKRCSFSA-N
Species of MetaboliteComponentSourceComments
Ballota limbata (IPNI:444966-1) whole plant (BTO:0001461) PubMed (15056960)
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.
lipoxygenase inhibitor  A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
ChEBI Ontology
Outgoing Relation(s)
ballotenic acid (CHEBI:65462) has role lipoxygenase inhibitor (CHEBI:35856)
ballotenic acid (CHEBI:65462) has role metabolite (CHEBI:25212)
ballotenic acid (CHEBI:65462) is a carbobicyclic compound (CHEBI:36785)
ballotenic acid (CHEBI:65462) is a diterpenoid (CHEBI:23849)
ballotenic acid (CHEBI:65462) is a monocarboxylic acid (CHEBI:25384)
ballotenic acid (CHEBI:65462) is a octahydronaphthalenes (CHEBI:138397)
ballotenic acid (CHEBI:65462) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[2-(2-oxotetrahydrofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
Registry NumbersSources
Reaxys:9804328Reaxys
Citations