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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 17:05:12 UTC
Update Date2020-10-09 21:04:10 UTC
HMDB IDHMDB0005897
Secondary Accession Numbers
  • HMDB05897
Metabolite Identification
Common 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 ). Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.
Structure
Data?1582752369
Synonyms
ValueSource
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
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namedihydrogenistein
CAS Registry Number21554-71-2
SMILES
OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-2790000000-26db6a2e908263b72058Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02mi-3941800000-9c483503cacf880146baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290000000-4644374ce6fee99f6a89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0970000000-1c5b97d1c0ef243d1effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1009-6910000000-ed3a33c853a4d6d2415bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-7a34d9e990680fc5c671Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-811724fce8e1beb6ab95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-5920000000-87f0fb1a3e444af53d71Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 864 details
UrineDetected and Quantified0.0215 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0904 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified0.124 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified21.7 +/- 6.0 (2.8 - 34.5) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.48 +/-0.27 (0.3 - 1.5) umol/mmol creatinineAdult (>18 years old)BothSoy consumption (ileostomies) details
Associated Disorders and Diseases
Disease References
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 IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023788
KNApSAcK IDNot Available
Chemspider ID8014076
KEGG Compound IDC14458
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9838356
PDB IDNot Available
ChEBI ID34707
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000475
References
Synthesis ReferenceInoue, Naoto. Studies on synthetic isoflavanones. III. Alkaline degradation of synthetic isoflavones and isoflavanones. Sci. Repts. Tohoku Univ., First Ser. (1961), 45(No. 1), 73-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chen L, Zhao X, Fang L, Games DE: Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. J Chromatogr A. 2007 Jun 22;1154(1-2):103-10. Epub 2007 Mar 15. [PubMed:17499260 ]
  2. Hwang CS, Kwak HS, Lim HJ, Lee SH, Kang YS, Choe TB, Hur HG, Han KO: Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):246-53. Epub 2006 Sep 11. [PubMed:16965913 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Dihydrogenistein → 3,4,5-trihydroxy-6-{[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
Dihydrogenistein → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
Dihydrogenistein → 6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Dihydrogenistein → [4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenyl]oxidanesulfonic aciddetails