CHEBI:65789 - 8α,19-dihydroxylabd-13E-ene-15-oic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 8α,19-dihydroxylabd-13E-ene-15-oic acid
ChEBI ID CHEBI:65789
ChEBI ASCII Name 8alpha,19-dihydroxylabd-13E-ene-15-oic acid
Definition A labdane diterpenoid that is labdane with a double bond at position 13 and is substituted by hydroxy groups at positions 8α and 19 and a carboxy group at position 15. Isolated from the aerial parts of Crassocephalum mannii, it exhibits inhibitory activity towards cyclooxygenases (COX-1 and COX-2).
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(12-17(22)23)6-7-16-19(3)10-5-9-18(2,13-21)15(19)8-11-20(16,4)24/h12,15-16,21,24H,5-11,13H2,1-4H3,(H,22,23)/b14-12+/t15-,16+,18-,19-,20+/m0/s1
InChIKey IYSBWLRXTOIYFZ-KBLZDMJYSA-N
SMILES [H][C@@]12CC[C@@](C)(O)[C@H](CC\C(C)=C\C(O)=O)[C@@]1(C)CCC[C@@]2(C)CO
Metabolite of Species Details
Crassocephalum mannii (IPNI:199508-1) 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) has role plant metabolite (CHEBI:76924)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) is a diol (CHEBI:23824)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) is a labdane diterpenoid (CHEBI:36770)
IUPAC Name
(2E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
Manual Xref Database
24713077 ChemSpider
View more database links
Citation Waiting for Citations Type Source
18473477 PubMed citation Europe PMC
Last Modified
24 October 2017