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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:05:49 UTC
Update Date2019-07-23 06:27:32 UTC
HMDB IDHMDB0038755
Secondary Accession Numbers
  • HMDB38755
Metabolite Identification
Common NameLicocoumarone
DescriptionLicocoumarone belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, licocoumarone is considered to be a flavonoid lipid molecule. Licocoumarone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Licocoumarone has been detected, but not quantified in, herbs and spices. This could make licocoumarone a potential biomarker for the consumption of these foods.
Structure
Data?1563863252
Synonyms
ValueSource
2-(2',4'-Dihydroxyphenyl)-6-hydroxy-5-isopentenyl-4-methoxybenzofuranChEBI
2-(3,4-Dihydroxyphenyl)-6-hydroxy-4-methoxy-5-prenylbenzofuranHMDB
4-[6-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9ciHMDB
Benzyl(2-hydroxyethyl)dimethylammonium hydroxideHMDB
Benzyl(2-hydroxyethyl)dimethylammonium, hydroxideHMDB
Chemical FormulaC20H20O5
Average Molecular Weight340.3698
Monoisotopic Molecular Weight340.13107375
IUPAC Name4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol
Traditional Namelicocoumarone
CAS Registry Number118524-14-4
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C20H20O5/c1-11(2)4-6-14-17(23)10-19-15(20(14)24-3)9-18(25-19)13-7-5-12(21)8-16(13)22/h4-5,7-10,21-23H,6H2,1-3H3
InChI KeyCNPMAFLUEHEXRE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • 2-phenylbenzofuran
  • Phenylbenzofuran
  • Benzofuran
  • Resorcinol
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP4.1ALOGPS
logP4.36ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.04ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.56 m³·mol⁻¹ChemAxon
Polarizability37.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-3059000000-688c32ebe43ea76cf897Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1000390000-b4ea00a39182594312f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-a068dcf2e78877d3d832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-4098000000-3107dca3fc1a784235dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6290000000-1967f6e59e9faf6d8e1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-1dc3540c6ad04b9c34f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-d066c3dd39217ce0a3d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3893000000-38241922e6c8195688dcSpectrum
Biological Properties
Cellular Locations
  • 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 IDFDB018169
KNApSAcK IDC00010076
Chemspider ID439849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound503731
PDB IDNot Available
ChEBI ID69098
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .