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CHEBI:138308 - kahweol

Default Structure
ChEBI IDCHEBI:138308
ChEBI Namekahweol
Stars
DefinitionA diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties.
Last Modified16 May 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H26O3
Net Charge0
Average Mass314.425
Monoisotopic Mass314.18819
SMILES[H][C@@]12CC[C@@H]3C[C@@]1(CC[C@]1([H])c4ccoc4C=C[C@@]21C)C[C@]3(O)CO
InChIInChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
InChIKeyJEKMKNDURXDJAD-HWUKTEKMSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Coffea arabica (ncbitaxon:13443) - PubMed (24209317) Isolated from green coffee oil. Strain: Catuai Amarelo variety
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
kahweol (CHEBI:138308) has role angiogenesis inhibitor (CHEBI:48422)
kahweol (CHEBI:138308) has role anti-inflammatory agent (CHEBI:67079)
kahweol (CHEBI:138308) has role antineoplastic agent (CHEBI:35610)
kahweol (CHEBI:138308) has role antioxidant (CHEBI:22586)
kahweol (CHEBI:138308) has role apoptosis inducer (CHEBI:68495)
kahweol (CHEBI:138308) has role plant metabolite (CHEBI:76924)
kahweol (CHEBI:138308) is a diterpenoid (CHEBI:23849)
kahweol (CHEBI:138308) is a furans (CHEBI:24129)
kahweol (CHEBI:138308) is a organic heteropentacyclic compound (CHEBI:38164)
kahweol (CHEBI:138308) is a primary alcohol (CHEBI:15734)
kahweol (CHEBI:138308) is a tertiary alcohol (CHEBI:26878)
IUPAC Names 
(1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-ol
(3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
Synonyms  Source
CCRIS 1521ChemIDplus
CCRIS-1521ChEBI
Manual XrefsDatabases
CPD-16468MetaCyc
FDB014295FooDB
HMDB0035602HMDB
KahweolWikipedia
Registry NumbersSources
CAS:6894-43-5ChemIDplus
Citations