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Cafestol

Common Name

Cafestol Description

Cafestol is found in arabica coffee. Cafestol is a constituent of coffee bean oil. Cafestol is present in boiled-type coffee beverages. Possesses hypercholesterolaemic activity. Diterpenoid constits. of coffee products are associated with cardiotoxic properties Cafestol is a diterpene moleclie present in coffee.Cafestol has been shown to exhibit apoptotic function (PMID 21334318 ).Cafestol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units. Structure

MOLSDFPDBSMILESInChI

Structure for HMDB35710 (Cafestol)

Synonyms

Value Source CafesterolHMDB CoffeolHMDB

Chemical Formlia

C20H28O3 Average Molecliar Weight

316.4345 Monoisotopic Molecliar Weight

316.203844762 IUPAC Name

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol Traditional Name

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol CAS Registry Number

469-83-0 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 Key

DNJVYWXIDISQRD-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as naphthofurans. These 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Naphthofurans Direct Parent

Naphthofurans Alternative Parents

  • Benzofurans
  • Tertiary alcohols
  • Heteroaromatic compounds
  • Furans
  • Cyclic alcohols and derivatives
  • 1,2-diols
  • Oxacyclic compounds
  • Primary alcohols
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

  • Food

    • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
  • apoptotic

    • Application

  • Nutrient
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point160 – 162 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.018 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity88.55 m3·mol-1ChemAxon Polarizability36.17 Å3ChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB014432 KNApSAcK ID

    C00003407 Chemspider ID

    2421 KEGG Compound ID

    C09066 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cafestol NuGOwiki Link

    HMDB35710 Metagene Link

    HMDB35710 METLIN ID

    Not Available PubChem Compound

    2516 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Xanthohumol

    References Synthesis Reference Not 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.. .

    PMID: 16936720