Kahweol (CHEM029500)

Record Information
Version1.0
Creation Date2016-05-26 01:12:13 UTC
Update Date2026-08-20 06:23:13 UTC
Accession NumberCHEM029500
Identification
Common NameKahweol
ClassSmall Molecule
Description
Kahweol is found in arabica coffee. Kahweol is present in boiled type-coffee beverages. May possess hypercholesterolaemic activity. Constit of coffee bean oil Kahweol is a diterpene molecule found in the beans of Coffea arabica. It is structurally related to cafestol
Contaminant Sources
  • FooDB Chemicals
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CCRIS 1521HMDB
CCRIS-1521HMDB
Chemical FormulaC20H26O3
Average Molecular Mass314.419 g/mol
Monoisotopic Mass314.188 g/mol
CAS Registry Number6894-43-5
IUPAC Name17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol
Traditional Name17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol
SMILESCC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3
InChI IdentifierInChI=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
InChI KeyJEKMKNDURXDJAD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Furan
  • Cyclic alcohol
  • 1,2-diol
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.97ALOGPS
logP2.55ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.69ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.51 m³·mol⁻¹ChemAxon
Polarizability35.08 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0035602
FooDB IDFDB014295
Phenol Explorer IDNot Available
KNApSAcK IDC00053387
BiGG IDNot Available
BioCyc IDCPD-16468
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkKahweol
Chemspider ID102755
ChEBI ID138308
PubChem Compound ID114778
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Oh JH, Lee JT, Yang ES, Chang JS, Lee DS, Kim SH, Choi YH, Park JW, Kwon TK: The coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK. Apoptosis. 2009 Nov;14(11):1378-86. doi: 10.1007/s10495-009-0407-x.
2. Kim HG, Kim JY, Hwang YP, Lee KJ, Lee KY, Kim DH, Kim DH, Jeong HG: The coffee diterpene kahweol inhibits tumor necrosis factor-alpha-induced expression of cell adhesion molecules in human endothelial cells. Toxicol Appl Pharmacol. 2006 Dec 15;217(3):332-41. Epub 2006 Oct 4.
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.