13,14,15,16-tetranorlabdane-8alpha,12,18-triol (CHEBI:66217)

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ChEBI Name	13,14,15,16-tetranorlabdane-8α,12,18-triol

ChEBI ID	CHEBI:66217

ChEBI ASCII Name	13,14,15,16-tetranorlabdane-8alpha,12,18-triol

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H30O3

Net Charge

Average Mass

270.40760

Monoisotopic Mass

270.21949

InChI

InChI=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

InChIKey

OSLJXGPVHCLGHU-XFIYOXNOSA-N

SMILES

C[C@@]1(O)CC[C@H]2[C@](C)(CO)CCC[C@]2(C)[C@H]1CCO

Metabolite of Species	Details
Crassocephalum mannii (IPNI:199508-1)	Found in aerial part (BTO:0001658). See: PubMed

Roles Classification
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.

ChEBI Ontology
Outgoing	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

Citation	Type	Source
18473477	PubMed citation	Europe PMC

Last Modified

25 November 2014