Structure Database (LMSD)

Common Name
Formononetin
Systematic Name
Synonyms
LM ID
LMPK12050037
Formula
C16H12O4
Exact Mass
Calculate m/z
268.07356
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum
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Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Isoflavonoids [PK1205]

Biological Context

Formononetin is an isoflavonoid phytoestrogenic compound found in soy-based foods and is the precursor of daidzein .1 It acts as an agonist of the aryl hydrocarbon receptor with an EC50 value of 0.13 µM.2 Formononetin has been reported to possess antitumor and antiviral activity.3,4

This information has been provided by Cayman Chemical

References

1. Yang, Y., Zhao, Y., Ai, X., et al. Formononetin suppresses the proliferation of human non-small cell lung cancer through induction of cell cycle arrest and apoptosis. Int. J. Clin. Exp. Pathol. 7(12), 8453-8461 (2014).
2. Wang, H., Zhang, D., Ge, M., et al. Formononetin inhibits enterovirus 71 replication by regulating COX-2/PGE2 expression. Virol. J. 12, 35 (2015).
3. Medjakovic, S., and Jungbauer, A. Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor. J. Steroid Biochem. Mol. Biol. 108(1-2), 171-177 (2008).
4. Patisaul, H.B., and Jefferson, W. The pros and cons of phytoestrogens. Front. Neuroendocrinol. 31(4), 400-419 (2010).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
HKQYGTCOTHHOMP-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
SMILES (Click to copy)
C1(O)=CC2OC=C(C3=CC=C(OC)C=C3)C(=O)C=2C=C1

Other Databases

Wikipedia
Formononetin
KEGG ID
C00858
HMDB ID
HMDB0005808
CHEBI ID
18088
METABOLOMICS ID
FLIA1ANS0001
PubChem CID
5280378
Cayman ID
17558

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 229.62
Topological Polar Surface Area 59.67
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 4.07
Molar Refractivity 76.24

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Updated at
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