Record Information
Version1.0
Creation date2011-09-21 00:34:44 UTC
Update date2017-10-05 10:34:17 UTC
Primary IDFDB023788
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrogenistein
DescriptionDihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260, 16965913) [HMDB]. Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.
CAS Number21554-71-2
Structure
Thumb
Synonyms
SynonymSource
2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
4',5,7-Trihydroxyisoflavan-4-oneChEBI
4',5,7-TrihydroxyisoflavanoneChEBI
4',5,7-Trihydroxy-isoflavanoneHMDB
2,3-dihydro-5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
4',5,7-trihydroxy-Isoflavanonehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP2.45ALOGPS
logP2.73ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O5
IUPAC name5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2
InChI KeyUQGVUYNHDKMLSE-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
Classification
Description Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanones
Alternative Parents
Substituents
  • Isoflavanone
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDihydrogenistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-2790000000-26db6a2e908263b72058Spectrum
Predicted GC-MSDihydrogenistein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02mi-3941800000-9c483503cacf880146baSpectrum
Predicted GC-MSDihydrogenistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290000000-4644374ce6fee99f6a89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0970000000-1c5b97d1c0ef243d1effSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1009-6910000000-ed3a33c853a4d6d2415bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-7a34d9e990680fc5c671Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-811724fce8e1beb6ab95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-5920000000-87f0fb1a3e444af53d71Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-031a5312b116bdf1aa4aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0960000000-6d1406b5d9d548a528a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0py3-9830000000-dc4e3eb841ad10a12b2eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d6b6f6391b4e9f4522f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0390000000-9cd64fafd3b06b9faac0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6980000000-881132da1830614a043eSpectrum
NMRNot Available
ChemSpider ID8014076
ChEMBL IDNot Available
KEGG Compound IDC14458
Pubchem Compound ID9838356
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05897
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID864
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference