Genistein
precursor
Showing entry for Genistein
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
External Links
- ChEBI
- 28088
- PubChem
- 5280961
- Chemistry Dashboard
- DTXSID5022308
- KNApSAcK
- C00002526
- MetaboLights
- MTBLC28088
- Phenol-Explorer
- 396
- FooDB (Compounds)
- FDB011828
- Exposome Explorer
- 3
- PeakForestCompound
- 000198
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 Phytochemical | Family | Class | Sub-class | |
---|---|---|---|---|
Genistin | Polyphenols | Flavonoids | Isoflavones | Show Food Phytochemical |
Genistein | Polyphenols | Flavonoids | Isoflavones | Show Food Phytochemical |
6''-O-Acetylgenistin | Polyphenols | Flavonoids | Isoflavones | Show Food Phytochemical |
6''-O-Malonylgenistin | Polyphenols | Flavonoids | Isoflavones | Show Food Phytochemical |
Biochanin A | Polyphenols | Flavonoids | Isoflavones | Show 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 ID | Source | Description | View |
---|---|---|---|
CE000011 | MassBank | LC-ESI-ITFT Spectrum - 35eV, unspecified | View Spectra |
CE000012 | MassBank | LC-ESI-ITFT Spectrum - 45eV, unspecified | View Spectra |
CE000013 | MassBank | LC-ESI-ITFT Spectrum - 55eV, unspecified | View Spectra |
CE000014 | MassBank | LC-ESI-ITFT Spectrum - -, unspecified | View Spectra |
OUF00238 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PB000881 | MassBank | LC-ESI-QTOF Spectrum - 15 eV, unspecified | View Spectra |
PB000882 | MassBank | LC-ESI-QTOF Spectrum - 25 eV, unspecified | View Spectra |
PB000884 | MassBank | LC-ESI-QTOF Spectrum - 40 eV, unspecified | View Spectra |
PB000885 | MassBank | LC-ESI-QTOF Spectrum - 55 eV, unspecified | View Spectra |
PB005712 | MassBank | LC-ESI-QTOF Spectrum - 10 eV, unspecified | View Spectra |
PB005713 | MassBank | LC-ESI-QTOF Spectrum - 15 eV, unspecified | View Spectra |
PB005714 | MassBank | LC-ESI-QTOF Spectrum - 20 eV, unspecified | View Spectra |
PB005715 | MassBank | LC-ESI-QTOF Spectrum - 25 eV, unspecified | View Spectra |
PB005721 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, unspecified | View Spectra |
PR040019 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, [M-H]- | View Spectra |
PR040020 | MassBank | LC-ESI-QTOF Spectrum - 30 eV, [M+H]+ | View Spectra |
PR040021 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+ | View Spectra |
PS040001 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS040002 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS040003 | ReSpect | N/A Spectrum - 30, [M+H]+ | View Spectra |
PS040004 | ReSpect | N/A Spectrum - 40, [M+H]+ | View Spectra |
TY000136 | MassBank | LC-ESI-ITTOF Spectrum - -, unspecified | View Spectra |
TY000137 | MassBank | LC-ESI-ITTOF Spectrum - -, unspecified | View Spectra |
UF416201 | MassBank | LC-ESI-ITFT Spectrum - 35, unspecified | View Spectra |
UF416202 | MassBank | LC-ESI-ITFT Spectrum - 55, unspecified | View Spectra |
UF416203 | MassBank | LC-ESI-ITFT Spectrum - 50, unspecified | View Spectra |
UF416204 | MassBank | LC-ESI-ITFT Spectrum - 80, unspecified | View Spectra |
UF416251 | MassBank | LC-ESI-ITFT Spectrum - 35, unspecified | View Spectra |
UF416252 | MassBank | LC-ESI-ITFT Spectrum - 55, unspecified | View Spectra |
UF416253 | MassBank | LC-ESI-ITFT Spectrum - 50, unspecified | View Spectra |
UF416254 | MassBank | LC-ESI-ITFT Spectrum - 80, unspecified | View Spectra |
Food Sources
Name | Group | |||
---|---|---|---|---|
Chickpea | Pulses and beans | Show | ||
Red clover | Pulses and beans | Publications | Show |
Food Sources of its Food Phytochemical(s)
Food Phytochemical | Food Source | Food Source Group | |||
---|---|---|---|---|---|
Genistein | Chickpea | Pulses and beans | Show | ||
Biochanin A | Chickpea | Pulses and beans | Show | ||
Genistein | Red clover | Pulses and beans | Publications | Show | |
Biochanin A | Red clover | Pulses and beans | Publications | Show | |
6''-O-Acetylgenistin | Soy bean | Soy and soy products | Show | ||
6''-O-Malonylgenistin | Soy bean | Soy and soy products | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Genistein | Genistein | human | plasma, serum, urine | unchanged | 5h-8h | 0.5-2 µmol/L | 10-30% | C15H10O5 | 270.052823422 | Publications | |||
Genistein | 4-Ethylphenol | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H10O | 122.073164942 | Detailed Intervention Studies | Publications | ||
Genistein | Dihydrogenistein | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C15H12O5 | 272.068473486 | Publications | |||
Genistein | Genistein 7-O-glucuronide | human | plasma, urine | host metabolism | 3h-5h | <20 nmol/L | Not Available | C21H18O11 | 446.0849114 | Publications | |||
Genistein | Genistein O-sulfate | Not Available | Not Available | host metabolism | Not Available | Not Available | Not Available | ||||||
Genistein | 6'-Hydroxy-O-desmethylangolensin | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C15H14O5 | 274.084123551 | Publications | |||
Genistein | Genistein 4',7-diglucuronide | human | plasma | host metabolism | 5h-8h | 50-200 nmol/L | Not Available | C27H26O17 | 622.116999377 | Detailed Intervention Studies | Publications | ||
Genistein | Genistein-7-O-glucuronide-4'-sulfate | human | plasma | host metabolism | 3h-5h | 50-200 nmol/L | Not Available | C21H17O14S | 525.034449981 | Publications | |||
Genistein | Genistein 4'-O-glucuronide | human | plasma | host metabolism | 3h-5h | <20 nmol/L | Not Available | C21H18O11 | 446.0849114 | Publications | |||
Genistein | Genistein 7-O-sulfate | human | plasma | host metabolism | 3h-5h | 50-200 nmol/L | Not Available | C15H10O8S | 350.009638456 | Publications | |||
Genistein | Genistein 4'-O-sulfate | human | plasma | host metabolism | 3h-5h | <20 nmol/L | Not Available | C15H10O8S | 350.009638456 | Publications | |||
Genistein | 3'-Hydroxygenistein | human | liver, urine | host metabolism | Not Available | Not Available | Not Available | C15H10O6 | 286.047738042 | Publications | |||
Genistein | 6-Hydroxygenistein | human | liver | host metabolism | Not Available | Not Available | Not Available | C15H10O6 | 286.047738042 | Publications | |||
Genistein | 8-hydroxy-genistein | human | liver, urine | host metabolism | Not Available | Not Available | Not Available | C15H10O6 | 286.047738042 | Publications | |||
Genistein | Genistein-4',7-disulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C15H10O11S2 | 429.96645349 | Publications | |||
Genistin | Genistein | human | plasma | gut microbiota metabolite | 5h-8h | 0.5-2 µmol/L | Not Available | C15H10O5 | 270.052823422 | Publications | |||
6''-O-Acetylgenistin | Genistein | human | Not Available | Not Available | Not Available | Not Available | Not Available | C15H10O5 | 270.052823422 | ||||
6''-O-Malonylgenistin | Genistein | human | Not Available | Not Available | Not Available | Not Available | Not Available | C15H10O5 | 270.052823422 | ||||
Biochanin A | Genistein | human | Not Available | Not Available | Not Available | Not Available | Not Available | C15H10O5 | 270.052823422 | Publications |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Genistein | Genistein | Age | Effect, clusters | Publications | ||
Genistein | Genistein | Genotype | Effect, clusters | Publications | ||
Genistein | Genistein | Microbiota | Effect, clusters | Publications | ||
Genistein | Genistein | Sex | Effect, clusters | Publications |