Glycitein (CHEM021709)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:33 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021709
Identification
Common NameGlycitein
ClassSmall Molecule
DescriptionA methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7,4'-Dihydroxy-6-methoxyisoflavoneChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-oneChEBI
Chemical FormulaC16H12O5
Average Molecular Mass284.267 g/mol
Monoisotopic Mass284.068 g/mol
CAS Registry Number40957-83-3
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Traditional Nameglycitein
SMILESCOC1=C(O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
InChI KeyDXYUAIFZCFRPTH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP3.35ALOGPS
logP2.57ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.92ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.17 m³·mol⁻¹ChemAxon
Polarizability28.81 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-cc30c39cbf8812a52470Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03kl-2319400000-b52790fd0e4c118732e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0917700000-5933de30c7285a663cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-3c1554bc5dca3cdb3846Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-c245729822931344a4e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0006-0190000000-4bba15c9cbb7f0e94476Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03dr-0290000000-e787f91d19d0f32fa54dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00kf-0090000000-b4f8659a75bd5b274388Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-cea55aa49f539e7744bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-9ae584c03a7824f82138Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-92e54bd765723d3af49eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-3eeade515966dbcb917bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-fc59669d8cbcb52a7d59Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-c245729822931344a4e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0190000000-4bba15c9cbb7f0e94476Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03dr-0290000000-e787f91d19d0f32fa54dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e6e8c814b71d8dfa0a6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-42d7e0eacd38b165f3d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3690000000-6349cd68b441d933fb98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-4f72582d90c392e49bc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-377795ff9f7a10037681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0490000000-9c9c282bae409459e339Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005781
FooDB IDFDB000698
Phenol Explorer ID398
KNApSAcK IDC00009392
BiGG IDNot Available
BioCyc IDCPD-7027
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlycitein
Chemspider ID4476508
ChEBI ID34778
PubChem Compound ID5317750
Kegg Compound IDC14536
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21848266
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24499298
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24950423
4. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.
5. Lang'at-Thoruwa, Caroline; Song, Tong T.; Hu, Jiang; Simons, Andrean L.; Murphy, Patricia A. A Simple Synthesis of 7,4'-Dihydroxy-6-methoxyisoflavone, Glycitein, the Third Soybean Isoflavone. Journal of Natural Products (2003), 66(1), 149-151.
6. Sirtori CR, Bosisio R, Pazzucconi F, Bondioli A, Gatti E, Lovati MR, Murphy P: Soy milk with a high glycitein content does not reduce low-density lipoprotein cholesterolemia in type II hypercholesterolemic patients. Ann Nutr Metab. 2002;46(2):88-92.
7. Simons AL, Renouf M, Hendrich S, Murphy PA: Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem. 2005 Nov 2;53(22):8519-25.