Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:36:41 UTC
Update Date2022-03-07 02:54:34 UTC
HMDB IDHMDB0035602
Secondary Accession Numbers
  • HMDB35602
Metabolite Identification
Common NameKahweol
DescriptionKahweol, also known as ccris 1521, 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. Kahweol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Kahweol.
Structure
Data?1563862744
Synonyms
ValueSource
CCRIS 1521ChEBI
CCRIS-1521ChEBI
Chemical FormulaC20H26O3
Average Molecular Weight314.4186
Monoisotopic Molecular Weight314.188194698
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
CAS Registry Number6894-43-5
SMILES
CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point143 - 143.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.57431661259
DarkChem[M-H]-168.8231661259
DeepCCS[M-2H]-203.05730932474
DeepCCS[M+Na]+178.28430932474
AllCCS[M+H]+177.832859911
AllCCS[M+H-H2O]+174.832859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-184.032859911
AllCCS[M+Na-2H]-183.832859911
AllCCS[M+HCOO]-183.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KahweolCC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C33476.2Standard polar33892256
KahweolCC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C32630.8Standard non polar33892256
KahweolCC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C32733.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Kahweol,1TMS,isomer #1CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C)C32838.6Semi standard non polar33892256
Kahweol,1TMS,isomer #2CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C)C32822.6Semi standard non polar33892256
Kahweol,2TMS,isomer #1CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C32824.4Semi standard non polar33892256
Kahweol,1TBDMS,isomer #1CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C(C)(C)C)C33111.8Semi standard non polar33892256
Kahweol,1TBDMS,isomer #2CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C(C)(C)C)C33102.3Semi standard non polar33892256
Kahweol,2TBDMS,isomer #1CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C33339.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kahweol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000m-0590000000-cbf3c432ffc87aed9e802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kahweol GC-MS (2 TMS) - 70eV, Positivesplash10-002f-9534800000-58b55eccff30839320c32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kahweol 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 - Kahweol 10V, Positive-QTOFsplash10-014i-0149000000-db23928410381e9a18f32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 20V, Positive-QTOFsplash10-00kb-0392000000-f4b88a6891473473ddf02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 40V, Positive-QTOFsplash10-0frw-5970000000-c8c248c27bb4efc9fdc02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 10V, Negative-QTOFsplash10-03di-0039000000-61fb732de24a5e6c886a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 20V, Negative-QTOFsplash10-03e9-0094000000-1c828fa69ffecae29c5b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 40V, Negative-QTOFsplash10-0uxr-1090000000-4bc978ebbf2a0ccf815c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 10V, Negative-QTOFsplash10-03di-0009000000-d8638daf32922c2274642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 20V, Negative-QTOFsplash10-03di-0019000000-f86639b6d0fdd901510d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 40V, Negative-QTOFsplash10-02t9-0093000000-15f5c908f4472d8d42152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 10V, Positive-QTOFsplash10-014i-0009000000-88e0e67fa31725f576fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 20V, Positive-QTOFsplash10-014l-3194000000-bb658b1aa87085b0e9e72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kahweol 40V, Positive-QTOFsplash10-001r-2930000000-0ebed8f5e58f9f6f24a42021-09-23Wishart 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 IDNot Available
KNApSAcK IDC00053387
Chemspider ID102755
KEGG Compound IDNot Available
BioCyc IDCPD-16468
BiGG IDNot Available
Wikipedia LinkKahweol
METLIN IDNot Available
PubChem Compound114778
PDB IDNot Available
ChEBI ID138308
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. 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. [PubMed:19768546 ]
  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. [PubMed:17097123 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .