Record Information
Version1.0
Creation date2010-04-08 22:11:16 UTC
Update date2018-05-29 18:28:18 UTC
Primary IDFDB014432
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCafestol
DescriptionCafestol is a diterpene molecule and is a constituent of coffee bean oil. It is found in boiled-type coffee beverages. Possesses hypercholesterolaemic activity. Diterpenoid constitsuents of coffee products are associated with cardiotoxic props.
CAS Number469-83-0
Structure
Thumb
Synonyms
SynonymSource
CafesterolHMDB
CoffeolHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.04ALOGPS
logP2.68ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.69ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.55 m³·mol⁻¹ChemAxon
Polarizability36.17 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H28O3
IUPAC name17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol
InChI IdentifierInChI=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
InChI KeyDNJVYWXIDISQRD-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
Classification
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
  • Benzofuran
  • 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
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.91%; H 8.92%; O 15.17%DFC
Melting PointMp 160-162° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -101 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-0491000000-8b320a709d91d7ff1ffeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0092-9434700000-2e50a5d7a6928201b152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0149000000-3a6b96b7f47db8b6922bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l2-0293000000-513aa1e79d3e41b9441aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ffx-7960000000-dd534580ddb824a054baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-e55c424af8a4bb5abfe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0094000000-f399341e0f5dd8ad74b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pvr-0090000000-f793b7dac060dcfa0106View in MoNA
ChemSpider ID2421
ChEMBL IDNot Available
KEGG Compound IDC09066
Pubchem Compound ID2516
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35710
CRC / DFC (Dictionary of Food Compounds) IDJQN12-S:JQN12-S
EAFUS IDNot Available
Dr. Duke IDCAFESTOL|CAFESTEROL
BIGG IDNot Available
KNApSAcK IDC00003407
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCafestol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
hypercholesterolemicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).