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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:30:27 UTC
Update Date2021-10-13 07:11:39 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. Glycycoumarin has been detected, but not quantified in, root vegetables. This could make glycycoumarin a potential biomarker for the consumption of these foods. Glycycoumarin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Glycycoumarin.
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point243.5 - 244.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.11 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
logP10(4.06) g/LALOGPS
logP10(4.11) g/LChemAxon
logS10(-4.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.82231661259
DarkChem[M-H]-189.53631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycycoumarinCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C14761.9Standard polar33892256
GlycycoumarinCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C13086.6Standard non polar33892256
GlycycoumarinCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C13551.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycycoumarin,1TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23294.6Semi standard non polar33892256
Glycycoumarin,1TMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23250.8Semi standard non polar33892256
Glycycoumarin,1TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23264.5Semi standard non polar33892256
Glycycoumarin,2TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23170.4Semi standard non polar33892256
Glycycoumarin,2TMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23170.0Semi standard non polar33892256
Glycycoumarin,2TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23166.7Semi standard non polar33892256
Glycycoumarin,3TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23154.5Semi standard non polar33892256
Glycycoumarin,1TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23561.7Semi standard non polar33892256
Glycycoumarin,1TBDMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23513.3Semi standard non polar33892256
Glycycoumarin,1TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23531.5Semi standard non polar33892256
Glycycoumarin,2TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23662.5Semi standard non polar33892256
Glycycoumarin,2TBDMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23629.1Semi standard non polar33892256
Glycycoumarin,2TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=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)O23638.1Semi standard non polar33892256
Glycycoumarin,3TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=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)O23781.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe3-1019000000-282ddd8e8c26f51571902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycycoumarin GC-MS (3 TMS) - 70eV, Positivesplash10-00vi-1000090000-c783ed22b161225cef622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycycoumarin 6V, Positive-QTOFsplash10-014i-0239000000-d9d32e4f7d08239440a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycycoumarin 6V, Negative-QTOFsplash10-014i-0139000000-a756c8040aba88b4cf472021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOFsplash10-014i-0019000000-e8f5e2687e52674237922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOFsplash10-02t9-2019000000-d045204802bd0020e4482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOFsplash10-014i-7192000000-e9862c4ef6e27eeb40172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOFsplash10-014i-0009000000-20b68087ed6e95096b142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOFsplash10-066r-0329000000-c3865e9020277be807822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOFsplash10-0a4i-4921000000-1394f8833dcd0fe74eec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOFsplash10-014i-0009000000-53fb202c32e20191eab92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOFsplash10-014r-0019000000-0adc5122ed4fb3bdacc42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOFsplash10-01bi-0029000000-174c1e96872b10850e452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOFsplash10-02t9-0009000000-ae0ab568c3686266872c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOFsplash10-03di-0019000000-726729680437cd2b03a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOFsplash10-015a-0093000000-7fbdb1164451861728272021-09-22Wishart 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 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
MarkerDB IDNot Available
Good Scents IDrw1866371
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.. .