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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:53 UTC
Update Date2020-02-26 21:43:49 UTC
HMDB IDHMDB0029515
Secondary Accession Numbers
  • HMDB29515
Metabolite Identification
Common NameLicoricone
DescriptionLicoricone belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, licoricone is considered to be a flavonoid lipid molecule. Licoricone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Licoricone has been detected, but not quantified in, herbs and spices. This could make licoricone a potential biomarker for the consumption of these foods.
Structure
Data?1582753429
Synonyms
ValueSource
2',7-Dihydroxy-4',6'-dimethoxy-3'-prenylisoflavoneHMDB
Chemical FormulaC22H22O6
Average Molecular Weight382.4065
Monoisotopic Molecular Weight382.141638436
IUPAC Name7-hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
Traditional Namelicoricone
CAS Registry Number51847-92-8
SMILES
COC1=C(CC=C(C)C)C(OC)=C(C(O)=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C22H22O6/c1-12(2)5-7-15-18(26-3)10-17(24)20(22(15)27-4)16-11-28-19-9-13(23)6-8-14(19)21(16)25/h5-6,8-11,23-24H,7H2,1-4H3
InChI KeyGGWMNTNDTRKETA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent4'-O-methylisoflavones
Alternative Parents
Substituents
  • 4p-o-methylisoflavone
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 - 251 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.85ALOGPS
logP4.14ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.46ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.87 m³·mol⁻¹ChemAxon
Polarizability40.67 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, Positivesplash10-0uxr-1009000000-f953546594b2ead04d5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2000590000-6cffd3e76f5dcfaa5345Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-822b3576c070e6511130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017i-2019000000-f8d6b72ee5ba4acdaed8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ds-9776000000-e4628c00357ae03bc280Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-f2c40fc3e934fc81fdd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0319000000-8d5bf687f8b9b9bf63b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-1921000000-84490d891846b01c6aa9Spectrum
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 IDFDB000651
KNApSAcK IDC00009443
Chemspider ID4477428
KEGG Compound IDC17765
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319013
PDB IDNot Available
ChEBI ID69094
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.. .