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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:13:19 UTC
Update Date2022-03-07 02:55:58 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. Isoglycycoumarin has been detected, but not quantified in, several different foods, such as red tea, herbal tea, teas (Camellia sinensis), herbs and spices, and black tea. This could make isoglycycoumarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoglycycoumarin.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.07 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.36331661259
DarkChem[M-H]-186.49431661259
DeepCCS[M+H]+187.65830932474
DeepCCS[M-H]-185.330932474
DeepCCS[M-2H]-219.27930932474
DeepCCS[M+Na]+194.49830932474
AllCCS[M+H]+188.732859911
AllCCS[M+H-H2O]+185.632859911
AllCCS[M+NH4]+191.632859911
AllCCS[M+Na]+192.432859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-190.732859911
AllCCS[M+HCOO]-190.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoglycycoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(C)O2)C1=C(O)C=C(O)C=C14133.0Standard polar33892256
IsoglycycoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(C)O2)C1=C(O)C=C(O)C=C13244.7Standard non polar33892256
IsoglycycoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(C)O2)C1=C(O)C=C(O)C=C13616.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoglycycoumarin,1TMS,isomer #1COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23149.0Semi standard non polar33892256
Isoglycycoumarin,1TMS,isomer #2COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23187.4Semi standard non polar33892256
Isoglycycoumarin,2TMS,isomer #1COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23116.6Semi standard non polar33892256
Isoglycycoumarin,1TBDMS,isomer #1COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23363.9Semi standard non polar33892256
Isoglycycoumarin,1TBDMS,isomer #2COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23402.1Semi standard non polar33892256
Isoglycycoumarin,2TBDMS,isomer #1COC1=C2CCC(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23522.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoglycycoumarin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frl-0219000000-c614735a9661f931610b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoglycycoumarin GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1010900000-1f962b4f55d68623d7362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoglycycoumarin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoglycycoumarin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 10V, Positive-QTOFsplash10-014i-0009000000-9e4a784ed72c7ac7f3e82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 20V, Positive-QTOFsplash10-03di-0019000000-80308f7d9f62e9ef99372016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 40V, Positive-QTOFsplash10-014i-4192000000-908466c14c51fcac53752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 10V, Negative-QTOFsplash10-014i-0009000000-7539f91ed290c81899672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 20V, Negative-QTOFsplash10-07vi-0219000000-78629abe4cb237c9d2c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 40V, Negative-QTOFsplash10-0a4i-6944000000-4e54b077f3c14a5b2c452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 10V, Negative-QTOFsplash10-014i-0009000000-53fb202c32e20191eab92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 20V, Negative-QTOFsplash10-016r-0009000000-640f60e784ed797e6bf12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 40V, Negative-QTOFsplash10-01b9-0129000000-bfb1ae3993fcc4f562d32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 10V, Positive-QTOFsplash10-014i-0009000000-c82ef03305a7d347ebd02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 20V, Positive-QTOFsplash10-014i-0009000000-66e85fbf0e406339e1222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoglycycoumarin 40V, Positive-QTOFsplash10-02or-0039000000-98c3a66e7ba8a30dc28a2021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1872241
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.. .