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Structure Database (LMSD)

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Common Name

Dihydrodaidzein

Systematic Name

7,4'-Dihydroxyisoflavanone

Synonyms

LM ID

LMPK12050447

Formula

C₁₅H₁₂O₄

Exact Mass

Calculate m/z

256.07356

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Isoflavonoids [PK1205]

Biological Context

Dihydrodaidzein is an active, estrogenic metabolite of daidzein.¹ It has vasodilatory action on rat isolated aortic rings at 1 µg/ml.² It stimulates the estrogen receptor-dependent growth of breast cancer MCF-7 cells at micromolar concentrations.³ Dihydrodaidzein is produced by the metabolism of daidzein in colonic bacteria and may be further metabolized to various bioactive compounds, including equol .^4,5

This information has been provided by Cayman Chemical

References

1. Chin-Disting, J.P.F., Fisher, L.J., Lewis, T.V., et al. The vascular activity of some isoflavone metabolites: Implications for a cardioprotective role. Brit. J. Pharmacol. 133(4), 595-605 (2001).

2. Franke, A.A., Lai, J.F., and Halm, B.M. Absorption, distribution, metabolism, and excretion of isoflavonoids after soy intake. Arch. Biochem. and Biophys. 559, 24-28 (2014).

3. Kinjo, J., Tsuchihashi, R., Morita, K., et al. Interactions of phytoestrogens with estrogen receptors α and β (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol. Pharm. Bull. 27(2), 185-188 (2004).

4. Rafii, F. The role of colonic bacteria in the metabolism of the natural isoflavone daidzin to equol. Metabolites 5(1), 56-73 (2015).

5. Schröder, D., Matthies, A., Engst, W., et al. Identification and expression of genes involved in the conversion of daidzein and genistein by the equol-forming bacterium Slackia isoflavoniconvertens. Appl. Environ. Microb. 79(11), 3494-3502 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Pericopsis (#53916)

Magnoliopsida (#3398)

Phytochemical examination of Pericopsis species,
J. Chem. Soc., Perkin Trans. 1, 1976

DOI: 10.1039/P19760000186

String Representations

InChiKey (Click to copy)

JHYXBPPMXZIHKG-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

SMILES (Click to copy)

C1(O)=CC2OCC(C3=CC=C(O)C=C3)C(=O)C=2C=C1

Other Databases

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 19

Rings 3

Aromatic Rings 2

Rotatable Bonds 1

Van der Waals Molecular Volume 225.86

Topological Polar Surface Area 68.83

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 4

logP 2.74

Molar Refractivity 69.27

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Created at

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Updated at

1st Aug 2025