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
Structure for Genistein
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 Phytohub
| Spectrum Type | Instrument Type | Technology | Ion Mode | Collision Energy | View | |
|---|---|---|---|---|---|---|
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Ei | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Ei | Not Available | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-APPI-QQ (API2000) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Positive | 5V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Negative | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-ITTOF (LCMS-IT-TOF) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-ITTOF (LCMS-IT-TOF) | Not Available | Negative | V | View Spectrum | |
| LC-MS/MS | ESI-TOF | Not Available | Negative | V | View Spectrum | |
| LC-MS/MS | ESI-TOF | Not Available | Negative | 20V | View Spectrum | |
| LC-MS/MS | ESI-TOF | Not Available | Negative | 50V | View Spectrum | |
| LC-MS/MS | ESI-TOF | Not Available | Negative | 40V | View Spectrum | |
| LC-MS/MS | ESI-TOF | From Sumner Library | Negative | V | View Spectrum | |
| LC-MS/MS | ESI-TOF | From Sumner Library | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 40V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 40V | View Spectrum |
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 |