Dihydrogenistein (CHEM021711)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:37 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021711
Identification
Common NameDihydrogenistein
ClassSmall Molecule
DescriptionA hydroxyisoflavanone comprising isoflavanone carrying three hydroxy substituents at positions 5, 7 and 4'.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass272.253 g/mol
Monoisotopic Mass272.068 g/mol
CAS Registry Number21554-71-2
IUPAC Name5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namedihydrogenistein
SMILESOC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-031a5312b116bdf1aa4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0960000000-6d1406b5d9d548a528a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0py3-9830000000-dc4e3eb841ad10a12b2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d6b6f6391b4e9f4522f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0390000000-9cd64fafd3b06b9faac0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6980000000-881132da1830614a043eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005897
FooDB IDFDB023788
Phenol Explorer IDNot Available
KNApSAcK IDC00052508
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8014076
ChEBI ID34707
PubChem Compound ID9838356
Kegg Compound IDC14458
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10527518
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15639088
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21626023
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22113864
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22493748
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22812014
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23542626
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24200780
9. Inoue, 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.
10. 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.
11. 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.