CHEBI:65463 - ballodiolic acid

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ChEBI Name ballodiolic acid
ChEBI ID CHEBI:65463
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H34O4
Net Charge 0
Average Mass 338.48160
Monoisotopic Mass 338.24571
InChI InChI=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
InChIKey BIRYTQFFNQPJBQ-UXWDVIHESA-N
SMILES [H]C(CO)(CCO)CC[C@@]1(C)[C@H](C)CC[C@@]2(C)C(=CCC[C@]12[H])C(O)=O
Metabolite of Species Details
Ballota limbata (IPNI:444966-1) Found in whole plant (BTO:0001461). 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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
9805708 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15056960 PubMed citation Europe PMC
17661429 PubMed citation Europe PMC
Last Modified
07 September 2017
General Comment
2012-11-19 The compound should not be confused with ballodiolic acid A: see Magn.Reson.Chem.2007;45:766-769.