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CHEBI:65462 - ballotenic acid

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:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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