Basic information
- Standard SMILES
O=c1c(-c2ccc(O)cc2)coc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc12- InChIKey
KYQZWONCHDNPDP-QNDFHXLGSA-N- Molecular formula
- C21H20O9
- Average molar mass
- 416.4 g/mol
- Monoisotopic mass
- 416.11073222
Overview
Daidzein 7-O-beta-D-glucoside is a glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic). It has a role as a plant metabolite. It is a 7-hydroxyisoflavones 7-O-beta-D-glucoside, a hydroxyisoflavone and a monosaccharide derivative. It is functionally related to a daidzein.
Names & identifiers
- Preferred name
- Daidzin
- IUPAC
- 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Names & synonyms
Daidzin552-66-9DaidzosideDaidzein 7-O-glucosideDaidzein 7-glucosideDaidzein-7-glucosidedaidzein 7-O-beta-D-glucoside4R2X91A5M53-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-oneCHEBI:422023-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
Show more names
7-O-glucosyl-4'-hydroxyisoflavone3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-4H-chromen-4-one3-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-oneRefChem:34445611-245-3MFCD000174667-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
Database identifiers
- CAS
552-66-9- PubChem CID
- 107971
- DTXSID
DTXSID00862180- ChEMBL
CHEMBL486422- ChEBI
CHEBI:42202- UNII
- 4R2X91A5M5
- EC Number
- 611-245-3
- Nikkaji
- J22.589D
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 644
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
LogP0.32
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point233 - 235 °C
Physical DescriptionSolid
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances interfering with the metabolism of ethyl alcohol, causing unpleasant side effects thought to discourage the drinking of alcoholic beverages. Alcohol deterrents are used in the treatment of alcoholism.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsCytoplasm
Related reactions
9 records
Linked notes
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