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Structure Database (LMSD)

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Common Name

Glycitein

Systematic Name

7,4'-Dihydroxy-6-methoxyisoflavone

Synonyms

LM ID

LMPK12050104

Formula

C₁₆H₁₂O₅

Exact Mass

Calculate m/z

284.068475

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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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

Glycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM.¹ It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor.² It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.^3,4

This information has been provided by Cayman Chemical

References

1. Yoshida, H., Teramoto, T., Ikeda, K., et al. Glycitein effect on suppressing the proliferation and stimulating the differentiation of osteoblastic MC3T3-E1 cells. Biosci. Biotechnol. Biochem. 65(5), 1211-1213 (2001).

2. Gutierrez-Zepeda, A., Santell, R., Wu, Z., et al. Soy isoflavone glycitein protects againstβamyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 6(54), (2005).

3. Pan, W., Ikeda, K., Takebe, M., et al. Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats. J. Nutr. 131(4), 1154-1158 (2001).

4. Song, T.T., Hendrich, S., and Murphy, P.A. Estrogenic activity of glycitein, a soy isoflavone. J. Agric. Food Chem. 47(4), 1607-1610 (1999).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Mildbraediodendron excelsum (#149663)

Magnoliopsida (#3398)

Isoflavonoids of Mildbraedeodendron excelsa,
Phytochemistry, 1975

DOI: 10.1016/S0031-9422(00)91117-8

String Representations

InChiKey (Click to copy)

DXYUAIFZCFRPTH-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

SMILES (Click to copy)

C1(O)=CC2OC=C(C3C=CC(O)=CC=3)C(=O)C=2C=C1OC

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 21

Rings 3

Aromatic Rings 3

Rotatable Bonds 2

Van der Waals Molecular Volume 238.41

Topological Polar Surface Area 79.90

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 5

logP 3.78

Molar Refractivity 77.91

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Created at

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Updated at

26th Jul 2025