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Record Information
Version5.0
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. Glycitein is found, on average, in the highest concentration within a few different foods, such as natto, soy beans (Glycine max), and miso and in a lower concentration in soy sauce, soy milk, and chickpeas (Cicer arietinum). Glycitein has also been detected, but not quantified in, several different foods, such as mung beans (Vigna radiata), dates (Phoenix dactylifera), garlics (Allium sativum), cashew nuts (Anacardium occidentale), and coffees (Coffea). This could make glycitein a potential biomarker for the consumption of these foods. Glycitein is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Glycitein.
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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available166.4431661259
DarkChem[M-H]-PredictedNot Available167.98531661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Glycitein,1TMS,#13084.139https://arxiv.org/abs/1905.12712
Glycitein,1TMS,#23120.3525https://arxiv.org/abs/1905.12712
Glycitein,2TMS,#12994.6577https://arxiv.org/abs/1905.12712
Glycitein,1TBDMS,#13303.9863https://arxiv.org/abs/1905.12712
Glycitein,1TBDMS,#23326.9294https://arxiv.org/abs/1905.12712
Glycitein,2TBDMS,#13481.4233https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-cc30c39cbf8812a524702017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03kl-2319400000-b52790fd0e4c118732e22017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0917700000-5933de30c7285a663ccc2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-3c1554bc5dca3cdb38462017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-c245729822931344a4e02017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0006-0190000000-4bba15c9cbb7f0e944762017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03dr-0290000000-e787f91d19d0f32fa54d2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00kf-0090000000-b4f8659a75bd5b2743882017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-cea55aa49f539e7744bc2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-9ae584c03a7824f821382017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-92e54bd765723d3af49e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-3eeade515966dbcb917b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-fc59669d8cbcb52a7d592017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-c245729822931344a4e02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0190000000-4bba15c9cbb7f0e944762017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03dr-0290000000-e787f91d19d0f32fa54d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e6e8c814b71d8dfa0a6a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-42d7e0eacd38b165f3d52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3690000000-6349cd68b441d933fb982016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-4f72582d90c392e49bc92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-377795ff9f7a100376812016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0490000000-9c9c282bae409459e3392016-08-03View Spectrum
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 ]