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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:13:19 UTC
Update Date2019-07-23 06:27:53 UTC
HMDB IDHMDB0038873
Secondary Accession Numbers
  • HMDB38873
Metabolite Identification
Common NameIsoglycycoumarin
DescriptionIsoglycycoumarin 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, isoglycycoumarin is considered to be a flavonoid lipid molecule. Isoglycycoumarin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isoglycycoumarin has been detected, but not quantified in, herbs and spices and tea. This could make isoglycycoumarin a potential biomarker for the consumption of these foods.
Structure
Data?1563863273
Synonyms
ValueSource
3-(2,4-Dihydroxyphenyl)-7,8-dihydro-5-methoxy-8,8-dimethyl-2H,6H-benzo[1,2-b:5,4-b']bipyran-2-one, 9ciHMDB
Chemical FormulaC21H20O6
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
IUPAC Name3-(2,4-dihydroxyphenyl)-5-methoxy-8,8-dimethyl-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one
Traditional Nameisoglycycoumarin
CAS Registry Number117038-82-1
SMILES
COC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(C)O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O6/c1-21(2)7-6-13-18(27-21)10-17-15(19(13)25-3)9-14(20(24)26-17)12-5-4-11(22)8-16(12)23/h4-5,8-10,22-23H,6-7H2,1-3H3
InChI KeyPHHAXWBLJNBVNS-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
  • Isoflav-3-enone skeleton
  • Hydroxyisoflavonoid
  • Pyranocoumarin
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Coumarin
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen 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 Point235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.98ALOGPS
logP3.71ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.86 m³·mol⁻¹ChemAxon
Polarizability38.99 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0frl-0219000000-c614735a9661f931610bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1010900000-1f962b4f55d68623d736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-9e4a784ed72c7ac7f3e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0019000000-80308f7d9f62e9ef9937Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4192000000-908466c14c51fcac5375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-7539f91ed290c8189967Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-0219000000-78629abe4cb237c9d2c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6944000000-4e54b077f3c14a5b2c45Spectrum
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 IDFDB018319
KNApSAcK IDC00010041
Chemspider ID24846665
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14187587
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .