Identification

PhytoHub ID
PHUB000225
Name
Genistein
Systematic Name
Not Available
Synonyms
  • 5,7,4'-Trihydroxyisoflavone
  • Genisteol
  • Prunetol
  • Sophoricol
CAS Number
Not Available
Average Mass
270.24
Monoisotopic Mass
270.052823422
Chemical Formula
C15H10O5
IUPAC Name
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
InChI Key
TZBJGXHYKVUXJN-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
SMILES
OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
Structure

Calculated Properties

Solubility (ALOGPS)
1.23e-01 g/l
LogS (ALOGPS)
-3.34
LogP (ALOGPS)
3.04
Hydrogen Acceptors
5
Hydrogen Donors
3
Rotatable Bond Count
1
Polar Surface Area
86.99000000000001
Refractivity
71.68289999999999
Polarizability
26.582127831950192
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.345613136233476
pKa (strongest acidic)
6.5462698153602235
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Isoflavones

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Flavonoid metabolites
Metabolite Sub-class
Isoflavones (parent, host and microbial metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
GenistinPolyphenolsFlavonoidsIsoflavonesShow Food Phytochemical
GenisteinPolyphenolsFlavonoidsIsoflavonesShow Food Phytochemical
6''-O-AcetylgenistinPolyphenolsFlavonoidsIsoflavonesShow Food Phytochemical
6''-O-MalonylgenistinPolyphenolsFlavonoidsIsoflavonesShow Food Phytochemical
Biochanin APolyphenolsFlavonoidsIsoflavonesShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Isoflavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Isoflav-2-enes
Direct Parent Name
Isoflavones
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzene and substituted derivatives", "Chromones", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Hydroxyisoflavonoids", "Organic oxides", "Organooxygen compounds", "Oxacyclic compounds", "Pyranones and derivatives", "Vinylogous acids"]
External Descriptor Annotations
["7-hydroxyisoflavones", "Isoflavonoids", "isoflavones"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Chromone", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyisoflavonoid", "Isoflavone", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Pyran", "Pyranone", "Vinylogous acid"]

Spectra from Online Resources

Record IDSourceDescriptionView
CE000011MassBankLC-ESI-ITFT Spectrum - 35eV, unspecifiedView Spectra
CE000012MassBankLC-ESI-ITFT Spectrum - 45eV, unspecifiedView Spectra
CE000013MassBankLC-ESI-ITFT Spectrum - 55eV, unspecifiedView Spectra
CE000014MassBankLC-ESI-ITFT Spectrum - -, unspecifiedView Spectra
OUF00238MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PB000881MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB000882MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB000884MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB000885MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB005712MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB005713MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB005714MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
PB005715MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB005721MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
PR040019MassBankLC-ESI-QTOF Spectrum - 30 eV, [M-H]-View Spectra
PR040020MassBankLC-ESI-QTOF Spectrum - 30 eV, [M+H]+View Spectra
PR040021MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+View Spectra
PS040001ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS040002ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS040003ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS040004ReSpectN/A Spectrum - 40, [M+H]+View Spectra
TY000136MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra
TY000137MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra
UF416201MassBankLC-ESI-ITFT Spectrum - 35, unspecifiedView Spectra
UF416202MassBankLC-ESI-ITFT Spectrum - 55, unspecifiedView Spectra
UF416203MassBankLC-ESI-ITFT Spectrum - 50, unspecifiedView Spectra
UF416204MassBankLC-ESI-ITFT Spectrum - 80, unspecifiedView Spectra
UF416251MassBankLC-ESI-ITFT Spectrum - 35, unspecifiedView Spectra
UF416252MassBankLC-ESI-ITFT Spectrum - 55, unspecifiedView Spectra
UF416253MassBankLC-ESI-ITFT Spectrum - 50, unspecifiedView Spectra
UF416254MassBankLC-ESI-ITFT Spectrum - 80, unspecifiedView Spectra

Spectra from Phytohub

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-0321900000-1dd6fcaf99898bd949df2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0321900000-1dd6fcaf99898bd949df2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0490000000-2922d094b504ca63625f2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3232900000-5532bb09d0ee2a1c2b072017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-014l-9600000000-04b546320e268d8172762012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-00kf-5910000000-7e265d1b4640f882195a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-0v4m-1960000000-7843ec8ae23314f881472012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-00di-0290000000-52ec910b223a3688fbc02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-00di-0190000000-4045f471e10774927fb02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-00di-0090000000-b593f863241cb83cbaa82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positivesplash10-00di-0190000000-0cd8d123608bd54f72142012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-00di-0090000000-9ce354d07dc39313259b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-5eb75a138568fa4ac8972012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fr6-2920000000-a32f6ae97952bb96de052012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0290000000-4592d557e739a114cbfa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-00di-0090000000-14ae481944ad1a1f7ca02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-014i-0090030000-a3400b0a77da6983528f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-6db4d2441911d696b1212017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-6db4d2441911d696b1212017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0900000000-ad50062f85b9c32e14262017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0910000000-6a694e60823635f667572017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-720c4e1f43db9f50b5892017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-0e3ca66534f635efb4d82017-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-3ca72bf3c489e8b068452017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-664850196c63c1380b4e2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5790000000-f3cf7e73e69ebaba09892017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-aa4506f67fa71b5e6f4e2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-f1f0ad0b45f461f988db2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3960000000-16725698ad6eee8f88dc2017-06-28View Spectrum

Food Sources

NameGroup
ChickpeaPulses and beansShow
Red cloverPulses and beans PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
GenisteinChickpeaPulses and beansShow
Biochanin AChickpeaPulses and beansShow
GenisteinRed cloverPulses and beans PublicationsShow
Biochanin ARed cloverPulses and beans PublicationsShow
6''-O-AcetylgenistinSoy beanSoy and soy productsShow
6''-O-MalonylgenistinSoy beanSoy and soy productsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Genistein Genisteinhumanplasma, serum, urineunchanged5h-8h0.5-2 ┬Ámol/L10-30%C15H10O5270.052823422 Publications
Genistein 4-Ethylphenolhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC8H10O122.073164942 Detailed Intervention Studies Publications
Genistein Dihydrogenisteinhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H12O5272.068473486 Publications
Genistein Genistein 7-O-glucuronidehumanplasma, urinehost metabolism3h-5h<20 nmol/LNot AvailableC21H18O11446.0849114 Publications
Genistein Genistein O-sulfateNot AvailableNot Availablehost metabolismNot AvailableNot AvailableNot Available
Genistein 6'-Hydroxy-O-desmethylangolensinhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H14O5274.084123551 Publications
Genistein Genistein 4',7-diglucuronidehumanplasmahost metabolism5h-8h50-200 nmol/LNot AvailableC27H26O17622.116999377 Detailed Intervention Studies Publications
Genistein Genistein-7-O-glucuronide-4'-sulfatehumanplasmahost metabolism3h-5h50-200 nmol/LNot AvailableC21H17O14S525.034449981 Publications
Genistein Genistein 4'-O-glucuronidehumanplasmahost metabolism3h-5h<20 nmol/LNot AvailableC21H18O11446.0849114 Publications
Genistein Genistein 7-O-sulfatehumanplasmahost metabolism3h-5h50-200 nmol/LNot AvailableC15H10O8S350.009638456 Publications
Genistein Genistein 4'-O-sulfatehumanplasmahost metabolism3h-5h<20 nmol/LNot AvailableC15H10O8S350.009638456 Publications
Genistein 3'-Hydroxygenisteinhumanliver, urinehost metabolismNot AvailableNot AvailableNot AvailableC15H10O6286.047738042 Publications
Genistein 6-Hydroxygenisteinhumanliverhost metabolismNot AvailableNot AvailableNot AvailableC15H10O6286.047738042 Publications
Genistein 8-hydroxy-genisteinhumanliver, urinehost metabolismNot AvailableNot AvailableNot AvailableC15H10O6286.047738042 Publications
Genistein Genistein-4',7-disulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC15H10O11S2429.96645349 Publications
Genistin Genisteinhumanplasmagut microbiota metabolite5h-8h0.5-2 ┬Ámol/LNot AvailableC15H10O5270.052823422 Publications
6''-O-Acetylgenistin GenisteinhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H10O5270.052823422
6''-O-Malonylgenistin GenisteinhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H10O5270.052823422
Biochanin A GenisteinhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H10O5270.052823422 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Genistein GenisteinAgeEffect, clusters Publications
Genistein GenisteinGenotypeEffect, clusters Publications
Genistein GenisteinMicrobiotaEffect, clusters Publications
Genistein GenisteinSexEffect, clusters Publications
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