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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:38:43 UTC
Update Date2022-03-07 02:57:10 UTC
HMDB IDHMDB0041726
Secondary Accession Numbers
  • HMDB41726
Metabolite Identification
Common NameDihydroglycitein
DescriptionDihydroglycitein belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Based on a literature review very few articles have been published on Dihydroglycitein.
Structure
Data?1563863695
SynonymsNot Available
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C16H14O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-7,12,17-18H,8H2,1H3
InChI KeyHEZSALBPROZVOO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent6-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 6-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Isoflavanone
  • Isoflavan
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.082 g/LALOGPS
logP2.83ALOGPS
logP2.22ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.2ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.16 m³·mol⁻¹ChemAxon
Polarizability28.88 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]+166.76931661259
DarkChem[M-H]-167.97431661259
DeepCCS[M+H]+171.66530932474
DeepCCS[M-H]-169.30730932474
DeepCCS[M-2H]-202.26430932474
DeepCCS[M+Na]+177.75930932474
AllCCS[M+H]+166.032859911
AllCCS[M+H-H2O]+162.332859911
AllCCS[M+NH4]+169.532859911
AllCCS[M+Na]+170.532859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-167.932859911
AllCCS[M+HCOO]-167.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydroglyciteinCOC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C13979.0Standard polar33892256
DihydroglyciteinCOC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C12728.9Standard non polar33892256
DihydroglyciteinCOC1=C(O)C=C2OCC(C(=O)C2=C1)C1=CC=C(O)C=C12868.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroglycitein,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OCC(C1=CC=C(O)C=C1)C2=O2815.8Semi standard non polar33892256
Dihydroglycitein,1TMS,isomer #2COC1=CC2=C(C=C1O)OCC(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O2866.4Semi standard non polar33892256
Dihydroglycitein,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OCC(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O2847.3Semi standard non polar33892256
Dihydroglycitein,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OCC(C1=CC=C(O)C=C1)C2=O3091.9Semi standard non polar33892256
Dihydroglycitein,1TBDMS,isomer #2COC1=CC2=C(C=C1O)OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O3118.3Semi standard non polar33892256
Dihydroglycitein,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O3330.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroglycitein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1790000000-9baf0d641b56745f1f6f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroglycitein GC-MS (2 TMS) - 70eV, Positivesplash10-066r-5925500000-780c4ddbf7fb7cd20efc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroglycitein 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 - Dihydroglycitein 10V, Positive-QTOFsplash10-000i-0390000000-66de58c2046baa329fc22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 20V, Positive-QTOFsplash10-0ap0-0930000000-0023c60a9be703f894e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 40V, Positive-QTOFsplash10-0691-6900000000-5dafef7415c9a02fb1492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 10V, Negative-QTOFsplash10-000i-0090000000-b11453be01d5cb82da782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 20V, Negative-QTOFsplash10-000i-0290000000-6716eae0f30409e858bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 40V, Negative-QTOFsplash10-0006-4980000000-df00c85321507ef53c162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 20V, Positive-QTOFsplash10-000i-0690000000-f628f5990a71a0f940832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 40V, Positive-QTOFsplash10-01bl-2930000000-c0bca912f824a949f30c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 10V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 20V, Negative-QTOFsplash10-0udi-0090000000-0b4423e1e3c90fe342872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroglycitein 40V, Negative-QTOFsplash10-000i-1890000000-b8f9fd198cbb432c81be2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 865 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 865 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029892
KNApSAcK IDNot Available
Chemspider ID35015224
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101101166
PDB IDNot Available
ChEBI ID174736
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]