Record Information
Version1.0
Creation date2010-04-08 22:13:33 UTC
Update date2019-11-26 03:15:48 UTC
Primary IDFDB018169
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Licocoumarone has been detected, but not quantified in, herbs and spices. This could make licocoumarone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licocoumarone.
CAS Number118524-14-4
Structure
Thumb
Synonyms
SynonymSource
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
4-[6-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9CIdb_source
Benzyl(2-hydroxyethyl)dimethylammonium Hydroxidebiospider
Licocoumaronedb_source
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
Chemical FormulaC20H20O5
IUPAC name4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C1
Average Molecular Weight340.3698
Monoisotopic Molecular Weight340.13107375
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.58%; H 5.92%; O 23.50%DFC
Melting PointMp 183-185°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLicocoumarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004m-3059000000-688c32ebe43ea76cf897Spectrum
Predicted GC-MSLicocoumarone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-1000390000-b4ea00a39182594312f9Spectrum
Predicted GC-MSLicocoumarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-000i-0958000000-99f252fd7a8eaa4f71182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000e-0956000000-590eda897b2930c2042d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-a068dcf2e78877d3d8322016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-4098000000-3107dca3fc1a784235dc2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6290000000-1967f6e59e9faf6d8e1b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-1dc3540c6ad04b9c34f62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-d066c3dd39217ce0a3d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3893000000-38241922e6c8195688dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-fd63e399cebf431bd2892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0059000000-33c2bcc8160b1f5289d32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0397000000-7dab7e62d2cd0a2825cf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-0069000000-8eb83bb6b0434d4cd3fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0091000000-847c3f386a48a65756312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-0091000000-4757bed94e115d81f1f92021-09-22View Spectrum
NMRNot Available
ChemSpider ID439849
ChEMBL IDCHEMBL611368
KEGG Compound IDNot Available
Pubchem Compound ID503731
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38755
CRC / DFC (Dictionary of Food Compounds) IDJVN94-B:LHF42-Y
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00010076
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference