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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-22 09:05:05 UTC
Update Date2020-10-09 21:04:02 UTC
HMDB IDHMDB0005781
Secondary Accession Numbers
  • HMDB05781
Metabolite Identification
Common NameGlycitein
DescriptionGlycitein 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. Thus, glycitein is considered to be a flavonoid lipid molecule. Glycitein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, glycitein is found, on average, in the highest concentration in a few different foods, such as miso, soy beans, and other soy products and in a lower concentration in soy milks, soy sauces, and soy yogurts. glycitein has also been detected, but not quantified in, pulses. This could make glycitein a potential biomarker for the consumption of these foods.
Structure
Data?1582752364
Synonyms
ValueSource
7,4'-Dihydroxy-6-methoxyisoflavoneChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-oneChEBI
Chemical FormulaC16H12O5
Average Molecular Weight284.267
Monoisotopic Molecular Weight284.068473486
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Traditional Nameglycitein
CAS Registry Number40957-83-3
SMILES
COC1=C(O)C=C2OC=C(C(=O)C2=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
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, Positivesplash10-0a4i-0490000000-cc30c39cbf8812a52470Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03kl-2319400000-b52790fd0e4c118732e2Spectrum
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
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0005 (0.00045- 0.00052) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00045 (0.00042-0.0005) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000352 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00640 +/- 0.0128 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0128 +/- 0.0272 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0224 +/- 0.0576 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0320 +/- 0.0784 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0384 +/- 0.0544 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.141 +/- 0.298 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineDetected and Quantified0.41 +/- 0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 398 details
UrineDetected and Quantified0.0169 +/- 0.0335 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.0231 +/- 0.0554 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.00879 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.106 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.147 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified0.67 +/- 0.26 umol/mmol creatinineAdult (>18 years old)BothSoy consumption ( ileostomies) details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ileostomy
  1. Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID398
FooDB IDFDB000698
KNApSAcK IDC00009392
Chemspider ID4476508
KEGG Compound IDC14536
BioCyc IDCPD-7027
BiGG IDNot Available
Wikipedia LinkGlycitein
METLIN IDNot Available
PubChem Compound5317750
PDB IDNot Available
ChEBI ID34778
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000470
References
Synthesis ReferenceLang'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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:12011578 ]
  2. 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. [PubMed:16248547 ]