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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:30:27 UTC
Update Date2019-07-23 06:26:00 UTC
HMDB IDHMDB0038225
Secondary Accession Numbers
  • HMDB38225
Metabolite Identification
Common NameGlycycoumarin
DescriptionGlycycoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, glycycoumarin is considered to be a flavonoid lipid molecule. Glycycoumarin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, glycycoumarin has been detected, but not quantified in, root vegetables. This could make glycycoumarin a potential biomarker for the consumption of these foods.
Structure
Data?1563863160
Synonyms
ValueSource
3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-oneChEBI
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ciHMDB
Chemical FormulaC21H20O6
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
IUPAC Name3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Traditional Nameglycycoumarin
CAS Registry Number94805-82-0
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3
InChI KeyNZYSZZDSYIBYLC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassHydroxyisoflavonoids
Direct ParentHydroxyisoflavonoids
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflav-3-enone skeleton
  • 7-hydroxycoumarin
  • Hydroxycoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point243.5 - 244.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.06ALOGPS
logP4.11ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.6ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.65 m³·mol⁻¹ChemAxon
Polarizability39.01 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, Positivesplash10-0fe3-1019000000-282ddd8e8c26f5157190Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00vi-1000090000-c783ed22b161225cef62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-e8f5e2687e5267423792Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-2019000000-d045204802bd0020e448Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7192000000-e9862c4ef6e27eeb4017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-20b68087ed6e95096b14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0329000000-c3865e9020277be80782Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4921000000-1394f8833dcd0fe74eecSpectrum
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
FoodDB IDFDB017468
KNApSAcK IDC00010040
Chemspider ID4476511
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317756
PDB IDNot Available
ChEBI ID69087
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tanaka Y, Kikuzaki H, Fukuda S, Nakatani N: Antibacterial compounds of licorice against upper airway respiratory tract pathogens. J Nutr Sci Vitaminol (Tokyo). 2001 Jun;47(3):270-3. [PubMed:11575586 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .