Dihydrogenistein

HCID 9838356CAS 21554-71-2

Substructure search Find similar structures

Basic information

Standard SMILES: O=C1c2c(O)cc(O)cc2OCC1c1ccc(O)cc1
InChIKey: UQGVUYNHDKMLSE-UHFFFAOYSA-N
Molecular formula: C15H12O5
Average molar mass: 272.25 g/mol
Monoisotopic mass: 272.06847348

Overview

Dihydrogenistein is a hydroxyisoflavanone comprising isoflavanone carrying three hydroxy substituents at positions 5, 7 and 4'. It has a role as a bacterial metabolite.

Names & identifiers

Preferred name: Dihydrogenistein
IUPAC: 5,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
English name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-
Molecular formula: C15H12O5
Molecular weight: 272.25

Names & synonyms

Dihydrogenistein21554-71-24',5,7-Trihydroxyisoflavan-4-one4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-5,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one5G1514R22RCHEBI:34707DTXSID809041535,7-Dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-oneRefChem:587753DTXCID101332037

Show more names

2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

112-295-45,7-Dihydroxy-3-(4-hydroxyphenyl)chroman-4-one5,7,4'-trihydroxyisoflavanone4',5,7-trihydroxyisoflavanone2'-DehydroxydalbergioidinOprea1_192406SCHEMBL678189CHEMBL209856

Database identifiers

CAS: 21554-71-2
PubChem CID: 9838356
DTXSID: DTXSID80904153
ChEMBL: CHEMBL209856
ChEBI: CHEBI:34707
UNII: 5G1514R22R
EC Number: 112-295-4
Nikkaji: J710.918K

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 87 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 20
Formal charge: 0
Complexity: 363

Experimental & physicochemical properties

Endocrine DisruptorsPotential endocrine disrupting compound

Physical DescriptionSolid

Physicochemical properties

Boiling point: 577.9 · 577.9±50.0 °C(Predicted)
Density: 1.485 · 1.485±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: Ethyl Acetate (Slightly), Methanol (Slightly)
pka: 7.52 · 7.52±0.40(Predicted)
form: Solid
color: Off-White to Pale Beige
biological source: synthetic
Stability: Hygroscopic, Light sensitive
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
InChIKey: UQGVUYNHDKMLSE-UHFFFAOYSA-N
SMILES: O1CC(C(=O)c3c1cc(cc3O)O)c2ccc(cc2)O
FDA UNII: 5 G1514R22R · 5G1514R22R
UNSPSC Code: 12352200 · 12352200
NACRES: 25 · NA.25
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: WGK 3
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313

Chemistry & industry

Pharmacology

Metabolism/MetabolitesDihydrogenistein has known human metabolites that include 2-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one.

Cellular LocationsMembrane

Applications

UsesDihydrogenistein is a derivative of Genistein (G350000), a compound that exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase.