EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66217 - 13,14,15,16-tetranorlabdane-8α,12,18-triol

ChEBI IDCHEBI:66217
ChEBI Name13,14,15,16-tetranorlabdane-8α,12,18-triol
Stars
ASCII Name13,14,15,16-tetranorlabdane-8alpha,12,18-triol
DefinitionA diterpenoid that is 13,14,15,16-tetranorlabdane substituted by hydroxy grousp at positions 8, 12 and 18. It has been isolated from the aerial parts of Crassocephalum mannii and has been shown to exhibit COX-1 and COX-2 activity.
Last Modified25 November 2014
DownloadsMolfile
FormulaC16H30O3
Net Charge0
Average Mass270.413
Monoisotopic Mass270.21949
SMILES[H][C@@]12CC[C@@](C)(O)[C@H](CCO)[C@@]1(C)CCC[C@@]2(C)CO
InChIInChI=1S/C16H30O3/c1-14(11-18)7-4-8-15(2)12(14)5-9-16(3,19)13(15)6-10-17/h12-13,17-19H,4-11H2,1-3H3/t12-,13+,14-,15-,16+/m0/s1
InChIKeyOSLJXGPVHCLGHU-XFIYOXNOSA-N
Species of MetaboliteComponentSourceComments
Crassocephalum mannii (IPNI:199508-1) aerial part (BTO:0001658) PubMed (18473477)
Roles Classification
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)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) has role plant metabolite (CHEBI:76924)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) is a diterpenoid (CHEBI:23849)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) is a tertiary alcohol (CHEBI:26878)
13,14,15,16-tetranorlabdane-8α,12,18-triol (CHEBI:66217) is a triol (CHEBI:27136)
IUPAC Name 
(1R,2R,4aR,5R,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol
Citations