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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:43:30 UTC
Update Date2021-09-14 15:29:57 UTC
HMDB IDHMDB0035710
Secondary Accession Numbers
  • HMDB35710
Metabolite Identification
Common NameCafestol
DescriptionCafestol, also known as coffeol, 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. Cafestol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cafestol has been detected, but not quantified in, a few different foods, such as arabica coffee, coffee, and coffee and coffee products. This could make cafestol a potential biomarker for the consumption of these foods. Cafestol is a diterpenoid molecule present in coffee beans. A typical bean of Coffea arabica contains about 0.4-0.7% cafestol by weight. Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee or Turkish coffee/Greek coffee. Cafestol has also shown anticarcinogenic properties in rats. Coffee consumption has been associated with a number of effects on health and cafestol has been proposed to produce these through a number of biological actions. Studies have shown that regular consumption of boiled coffee increases serum cholesterol whereas filtered coffee does not. Thus cafestol can increase cholesterol synthesis. It is one of the compounds that may be responsible for proposed biological and pharmacological effects of coffee. Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis.
Structure
Data?1563862759
Synonyms
ValueSource
CafesterolHMDB
CoffeolHMDB
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol
Traditional Name17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol
CAS Registry Number469-83-0
SMILES
CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3
InChI Identifier
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
InChI KeyDNJVYWXIDISQRD-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
  • 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP10(3.04) g/LALOGPS
logP10(2.68) g/LChemAxon
logS10(-4.2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.54431661259
DarkChem[M-H]-168.46631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CafestolCC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C33142.0Standard polar33892256
CafestolCC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C32639.0Standard non polar33892256
CafestolCC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C32756.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cafestol,1TMS,isomer #1CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C)C32850.3Semi standard non polar33892256
Cafestol,1TMS,isomer #2CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C)C32828.8Semi standard non polar33892256
Cafestol,2TMS,isomer #1CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C32826.4Semi standard non polar33892256
Cafestol,1TBDMS,isomer #1CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C(C)(C)C)C33119.3Semi standard non polar33892256
Cafestol,1TBDMS,isomer #2CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C(C)(C)C)C33103.2Semi standard non polar33892256
Cafestol,2TBDMS,isomer #1CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C33353.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cafestol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-0491000000-8b320a709d91d7ff1ffe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cafestol GC-MS (2 TMS) - 70eV, Positivesplash10-0092-9434700000-2e50a5d7a6928201b1522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cafestol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 10V, Positive-QTOFsplash10-014i-0149000000-3a6b96b7f47db8b6922b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 20V, Positive-QTOFsplash10-00l2-0293000000-513aa1e79d3e41b9441a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 40V, Positive-QTOFsplash10-0ffx-7960000000-dd534580ddb824a054ba2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 10V, Negative-QTOFsplash10-014i-0039000000-e55c424af8a4bb5abfe52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 20V, Negative-QTOFsplash10-014i-0094000000-f399341e0f5dd8ad74b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 40V, Negative-QTOFsplash10-0pvr-0090000000-f793b7dac060dcfa01062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 10V, Positive-QTOFsplash10-014i-0009000000-7a45cf767c0416b1cc052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 20V, Positive-QTOFsplash10-00ke-0093000000-4524e55457ed7eb794712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 40V, Positive-QTOFsplash10-06rj-3951000000-2c42c767d2b59afdb32e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 10V, Negative-QTOFsplash10-014i-0009000000-d337ec43015bf5d00be62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 20V, Negative-QTOFsplash10-014i-0019000000-9e44ccfae91118d36eab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cafestol 40V, Negative-QTOFsplash10-014r-0093000000-f1f44de6b38a9b8fea792021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014432
KNApSAcK IDC00003407
Chemspider ID2421
KEGG Compound IDC09066
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCafestol
METLIN IDNot Available
PubChem Compound2516
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Choi MJ, Park EJ, Oh JH, Min KJ, Yang ES, Kim YH, Lee TJ, Kim SH, Choi YH, Park JW, Kwon TK: Cafestol, a coffee-specific diterpene, induces apoptosis in renal carcinoma Caki cells through down-regulation of anti-apoptotic proteins and Akt phosphorylation. Chem Biol Interact. 2011 Apr 25;190(2-3):102-8. doi: 10.1016/j.cbi.2011.02.013. Epub 2011 Feb 18. [PubMed:21334318 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .