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CHEBI:65463 - ballodiolic acid

ChEBI IDCHEBI:65463
ChEBI Nameballodiolic 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 5-hydroxy-3-(hydroxymethyl)pentyl 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
FormulaC20H34O4
Net Charge0
Average Mass338.488
Monoisotopic Mass338.24571
SMILES[H]C(CO)(CCO)CC[C@@]1(C)[C@H](C)CC[C@@]2(C)C(C(=O)O)=CCC[C@@]21[H]
InChIInChI=1S/C20H34O4/c1-14-7-10-20(3)16(18(23)24)5-4-6-17(20)19(14,2)11-8-15(13-22)9-12-21/h5,14-15,17,21-22H,4,6-13H2,1-3H3,(H,23,24)/t14-,15?,17-,19+,20+/m1/s1
InChIKeyBIRYTQFFNQPJBQ-UXWDVIHESA-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)
ballodiolic acid (CHEBI:65463) has role lipoxygenase inhibitor (CHEBI:35856)
ballodiolic acid (CHEBI:65463) has role metabolite (CHEBI:25212)
ballodiolic acid (CHEBI:65463) is a carbobicyclic compound (CHEBI:36785)
ballodiolic acid (CHEBI:65463) is a diol (CHEBI:23824)
ballodiolic acid (CHEBI:65463) is a diterpenoid (CHEBI:23849)
ballodiolic acid (CHEBI:65463) is a monocarboxylic acid (CHEBI:25384)
ballodiolic acid (CHEBI:65463) is a octahydronaphthalenes (CHEBI:138397)
IUPAC Name 
(4aR,5S,6R,8aR)-5-[5-hydroxy-3-(hydroxymethyl)pentyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
Registry NumbersSources
Reaxys:9805708Reaxys
Citations