EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65463 - ballodiolic acid

Default Structure
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:
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)
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