LIPID MAPS

Structure Database (LMSD)

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Common Name

3'-Hydroxydaidzein

Systematic Name

Synonyms

LM ID

LMPK12050055

Formula

C₁₅H₁₀O₅

Exact Mass

Calculate m/z

270.052825

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View NP-MRD ID(NMR) spectrum

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Isoflavonoids [PK1205]

Biological Context

3',4',7-Trihydroxyisoflavone is a natural isoflavonoid that has antioxidant activity.¹ It can be produced by the metabolism of daidzein or daidzin .^2,3 3',4',7-Trihydroxyisoflavone inhibits several signaling pathways in cells, including tyrosinase-mediated melanin formation (IC50 = 5.2 µM), casein kinase II-mediated phosphorylation of 60S acidic ribosomal P proteins, and cyclin-dependent, kinase-regulated cell proliferation.^4,5,6

This information has been provided by Cayman Chemical

References

1. Choi, K.-Y., Kim, T.-j., Koh, S.-K., et al. A-ring ortho-specific monohydroxylation of daidzein by cytochrome P450s of Nocardia farcinica IFM10152. Biotechnol. J. 4(11), 1586-1595 (2009).

2. Komiyama, K., Funayama, S., Anraku, Y., et al. Isolation of isoflavonoids possessing antioxidant activity from the fermentation broth of Streptomyces sp. J. Antibiot. (Tokyo) 42(9), 1344-1349 (1989).

3. Lee, D.E., Lee, K.Q., Song, N.R., et al. 7,3',4'-Trihydroxyisoflavone inhibits epidermal growth factor-induced proliferation and transformation of JB6 P+ mouse epidermal cells by suppressing cyclin-dependent kinases and phosphatidylinositol 3-kinase. The Journal of Biological Chemisty 285(28), 21458-21466 (2010).

4. Maekawa, T., Kosuge, S., Sakamoto, S., et al. Biochemical characterization of 60S acidic ribosomal P proteins associated with CK-II from bamboo shoots and potent inhibitors of their phosphorylation in vitro. Biol. Pharm. Bull. 22(7), 667-673 (1999).

5. Park, J.-S., Kim, D.H., Lee, J.K., et al. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg. Med. Chem. Lett. 20(3), 1162-1164 (2010).

6. Yasuda, T., and Ohsawa, K. Urinary metabolites of daidzin orally administered in rats. Biol. Pharm. Bull. 21(9), 953-957 (1998).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

DDKGKOOLFLYZDL-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H

SMILES (Click to copy)

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

Other Databases

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

PDB ID

GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 20

Rings 3

Aromatic Rings 3

Rotatable Bonds 1

Van der Waals Molecular Volume 221.11

Topological Polar Surface Area 90.90

Hydrogen Bond Donors 3

Hydrogen Bond Acceptors 5

logP 3.48

Molar Refractivity 73.02

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