Structure Database (LMSD)
Common Name
Calycosin
Systematic Name
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Synonyms
- 3'-Hydroxyformononetin
3D model of Calycosin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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