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CHEBI:138308 - kahweol

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:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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-1521ChEBI
CCRIS 1521ChemIDplus
Manual XrefsDatabases
FDB014295FooDB
CPD-16468MetaCyc
HMDB0035602HMDB
KahweolWikipedia
Registry NumbersSources
CAS:6894-43-5ChemIDplus
Citations