CHEBI:138308 - kahweol

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ChEBI Name kahweol
ChEBI ID CHEBI:138308
Definition A diterpenoid with formula C20H26O3, isolated from the beans of Coffea arabica. It exhibits antioxidant, anti-inflammatory, anti-angiogenesis and anti-proliferative properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H26O3
Net Charge 0
Average Mass 314.419
Monoisotopic Mass 314.18819
InChI InChI=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
InChIKey JEKMKNDURXDJAD-HWUKTEKMSA-N
SMILES [C@]123[C@]([H])([C@@]4(C)[C@@](C5=C(C=C4)OC=C5)(CC1)[H])CC[C@H](C2)[C@@](C3)(O)CO
Metabolite of Species Details
Coffea arabica (NCBI:txid13443) Isolated from green coffee oil. of strain Catuai Amarelo variety See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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.
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
CCRIS 1521 ChemIDplus
CCRIS-1521 ChEBI
Manual Xrefs Databases
CPD-16468 MetaCyc
FDB014295 FooDB
HMDB0035602 HMDB
Kahweol Wikipedia
View more database links
Registry Number Type Source
6894-43-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17590492 PubMed citation Europe PMC
21858104 PubMed citation Europe PMC
24209317 PubMed citation Europe PMC
27424123 PubMed citation Europe PMC
27748804 PubMed citation Europe PMC
27871156 PubMed citation Europe PMC
30205135 PubMed citation Europe PMC
3612687 PubMed citation Europe PMC
Last Modified
16 May 2019