CHEBI:3291 - cafestol

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ChEBI Name cafestol
ChEBI ID CHEBI:3291
Definition An organic heteropentacyclic compound and furan diterpenoid with formula C20H28O3 obtained from the unsaponifiable fraction of coffee oil (a lipid fraction obtained from coffee beans by organic solvent extraction).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H28O3
Net Charge 0
Average Mass 316.435
Monoisotopic Mass 316.204
InChI InChI=1S/C20H28O3/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/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
InChIKey DNJVYWXIDISQRD-HWUKTEKMSA-N
SMILES [C@]123[C@]([H])([C@@]4(C)[C@@](C5=C(CC4)OC=C5)(CC1)[H])CC[C@H](C2)[C@@](C3)(O)CO
Metabolite of Species Details
Coffea arabica (NCBI:13443) See: Clarke, R.J. and Macrae, R. (2013). Coffee Volume 1: Chemistry. Springer, New York. ISBN 978-9401086936
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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ChEBI Ontology
Outgoing cafestol (CHEBI:3291) has role angiogenesis inhibitor (CHEBI:48422)
cafestol (CHEBI:3291) has role anti-inflammatory agent (CHEBI:67079)
cafestol (CHEBI:3291) has role antineoplastic agent (CHEBI:35610)
cafestol (CHEBI:3291) has role antioxidant (CHEBI:22586)
cafestol (CHEBI:3291) has role apoptosis inducer (CHEBI:68495)
cafestol (CHEBI:3291) has role hypoglycemic agent (CHEBI:35526)
cafestol (CHEBI:3291) has role plant metabolite (CHEBI:76924)
cafestol (CHEBI:3291) is a diterpenoid (CHEBI:23849)
cafestol (CHEBI:3291) is a furans (CHEBI:24129)
cafestol (CHEBI:3291) is a organic heteropentacyclic compound (CHEBI:38164)
cafestol (CHEBI:3291) is a primary alcohol (CHEBI:15734)
cafestol (CHEBI:3291) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(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-dien-17-ol
Synonym Source
(−)-cafestol ChEBI
Database Links Databases
C00003407 KNApSAcK
C09066 KEGG COMPOUND
Cafestol Wikipedia
HMDB0035710 HMDB
US4692534 Patent
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Registry Numbers Types Sources
33406 Reaxys Registry Number Reaxys
469-83-0 CAS Registry Number KEGG COMPOUND
469-83-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
29 August 2017