cafestol
(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
Molecular Identity
cafestol
(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
PubChem CID: 108052
Cafestol is 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). It has a role as an antioxidant, a hypoglycemic agent, an antineoplastic agent, an angiogenesis inhibitor, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a primary alcohol, a diterpenoid, a member of furans, a tertiary alcohol and an organic heteropentacyclic compound.
2D Structure
Properties
C20H28O3
Molecular Formula
316.40
Molecular Weight
g/mol
316.2038
Exact Mass
Da
3.3
XLogP
Drug-like (Lipinski: < 5)
53.6
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
507
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
cafestol469-83-0cafesterolCCRIS 1518AC465T6Q6WDTXSID3040986CHEBI:3291(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-ol5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-, (3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))-(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-olRefChem:122657DTXCID1020986MFCD01075769Cafestol (>85%)UNII-AC465T6Q6W
Data from PubChem (NCBI)
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