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

ChEBI IDCHEBI:65789
ChEBI Name8α,19-dihydroxylabd-13E-ene-15-oic acid
Stars
ASCII Name8alpha,19-dihydroxylabd-13E-ene-15-oic acid
DefinitionA 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).
Last Modified24 October 2017
DownloadsMolfile
FormulaC20H34O4
Net Charge0
Average Mass338.488
Monoisotopic Mass338.24571
SMILES[H][C@@]12CC[C@@](C)(O)[C@H](CC/C(C)=C/C(=O)O)[C@@]1(C)CCC[C@@]2(C)CO
InChIInChI=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
InChIKeyIYSBWLRXTOIYFZ-KBLZDMJYSA-N
Species of MetaboliteComponentSourceComments
Crassocephalum mannii (IPNI:199508-1) whole plant (BTO:0001461) PubMed (18473477)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
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 diol (CHEBI:23824)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) is a labdane diterpenoid (CHEBI:36770)
8α,19-dihydroxylabd-13E-ene-15-oic acid (CHEBI:65789) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
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 XrefsDatabases
24713077ChemSpider
Citations