Structure Database (LMSD)

Common Name
Calycosin
Systematic Name
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Synonyms
  • 3'-Hydroxyformononetin
LM ID
LMPK12050056
Formula
Exact Mass
Calculate m/z
284.068475
Status
Curated

Classification

Biological Context

Calycosin is an isoflavone and phytoestrogen with diverse biological activities.1,2,3,4,5,6 It is an estrogen receptor (ER) partial agonist that inhibits 17β-estradiol binding to ERα and ERβ (IC50s = 83.14 and 40.38 μM, respectively).1 Calycosin induces tube formation by human umbilical vein endothelial cells (HUVECs) in a Matrigel™ assay and angiogenesis in zebrafish via activation of ERs and ERK1/2. It has antiplasmodial and antiprotozoal activities, reducing the growth of the poW and Dd2 strains of P. falciparum (IC50s = 4.2 and 9.8 μg/ml, respectively) and exhibiting selective toxicity for T. brucei brucei over Vero cells (IC50s = 12.7 and 159 μM, respectively).2,3 Calycosin scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals in a cell-free assay and inhibits xanthine/xanthine oxidase-induced toxicity in PC12 cells (EC50 = 50 ng/ml).4 In vivo, calycosin (12.5 and 25 mg/kg) reduces alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activity, triglyceride accumulation, and hepatic fibrosis in a mouse model of non-alcoholic steatohepatitis (NASH).5 It also decreases infarct volume and brain edema in a rat model of focal cerebral ischemia and reperfusion injury.6

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/
Baptisia lecontei (#1969222)
Magnoliopsida (#3398)
The identification of twenty-three 5-deoxy- and ten 5-hydroxy-flavonoids from Baptisia lecontei (leguminosae),
Phytochemistry, 1968

String Representations

InChiKey (Click to copy)
ZZAJQOPSWWVMBI-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
SMILES (Click to copy)
C1(O)=CC2OC=C(C3C=CC(OC)=C(O)C=3)C(=O)C=2C=C1

Other Databases

Wikipedia
KEGG 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
29th Jul 2025