CAS 552-66-9|Daidzein 7-O-glucoside|7-O-B-D-GLUCOPYRANOSIDE|Daidzein-7-glucoside|Daidzoside|daidzein 7-O-β-D-glucoside|7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one|3-(4-hy...

General Information

Structure

Molecular Formula

C₂₁H₂₀O₉

Molecular Mass

416.3781

Exact Mass

416.11073222

Charge

InChI

InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1

InChIKey

KYQZWONCHDNPDP-QNDFHXLGSA-N

Canonic Smiles

OC[C@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O

Isomeric Smiles

OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(O)cc1

Calculated Properties

JChem

Acid pKa

8.962957

H Acceptors

H Donor

LogD (pH = 5.5)

0.46222103

LogD (pH = 7.4)

0.45072386

Log P

0.46236962

Molar Refractivity

101.8464

Polarizability

40.17439

Polar Surface Area

145.91

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.71

LOG S

-2.8

Solubility (Water)

6.61e-01 g/l

Data Source

Names and Identifiers

Synonyms

7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneDaidzein 7-glucosideDaidzein-7-glucosideDaidzoside7-O-B-D-GLUCOPYRANOSIDEDaidzein 7-O-glucoside7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one4',7-DihydroxyisoflavoneDaidzinDaidzein-7-O-β-D-glucopyranosideDaidzin

IUPAC Traditional name

daidzein 7-O-β-D-glucoside daidzin 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

IUPAC name

3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Names and Identifiers

Registration numbers

CAS Number

552-66-9

MDL Number

MFCD00017466

PubChem SID

1609653312485832346505206

Beilstein Number

59741

EC Number

207-635-4

PubChem CID

107971

Registration numbers

Properties

Pharmacology Properties

Gene Information

mouse ... Aldh1a2(19378), Maoa(17161)rat ... Aldh1a2(116676)

Mechanism of Action

Antidipsotropic

Product Information

Purity

≥95.0% (HPLC)

≥98.0% (HPLC)

Empirical Formula (Hill Notation)

C21H20O9

Shelf Life

(limited shelf life, expiry date on the label)

Grade

analytical standard

Application(s)

Cancer preventive and an alcohol dependency treatment

Isol. from soya bean meal, roots of Pueraria lobata and shoots of Piptanthus nepalensis. Also from Baptisia spp., Glycine max, Medicago sativa, Thermopsis spp. and others in Leguminosae

Physical Property

Apperance

Powder

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB02115

Drug information: experimental

Sigma Aldrich

42926

Biochem/physiol Actions
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1

30408

Biochem/physiol Actions
Daidzin is an isoflavone reported to have anti-oxidant, anti-carcinogenic, and anti-artherosclerotic activities. Daidzin is the major active component of the traditional Chinese medicine (TCM) derived from radix puerariae (Kudzu) that is commonly used to treat alcohol abuse. Daidzin is a potent and selective inhibitor of mitochondrial aldehyde dehydrogenase 2 (ALDH-2).
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 30408.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Molecule Details

References

PubChem Literature

From Data Sources

• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

daidzein 7-O-β-D-glucoside daidzin 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

IUPAC name

3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Registration numbers

CAS Number

552-66-9

MDL Number

MFCD00017466

PubChem SID

1609653312485832346505206

Beilstein Number

EC Number

PubChem CID

Molecule Details

DB02115

Drug information: experimental

Sigma Aldrich

42926

Biochem/physiol Actions
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1

30408

References

PubChem Literature

From Data Sources

• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

mouse ... Aldh1a2(19378), Maoa(17161)rat ... Aldh1a2(116676)

Mechanism of Action

Antidipsotropic

Product Information

Purity

≥95.0% (HPLC)

≥98.0% (HPLC)

Empirical Formula (Hill Notation)

C21H20O9

Shelf Life

(limited shelf life, expiry date on the label)

Grade

analytical standard

Application(s)

Cancer preventive and an alcohol dependency treatment

Isol. from soya bean meal, roots of Pueraria lobata and shoots of Piptanthus nepalensis. Also from Baptisia spp., Glycine max, Medicago sativa, Thermopsis spp. and others in Leguminosae

Physical Property

Apperance

Powder

Molecule

ID:1876