Structure Database (LMSD)

Common Name
Coumestrol
Systematic Name
3,9-Dihydroxycoumestan
Synonyms
  • Cumestrol
LM ID
LMPK12090018
Formula
C15H8O5
Exact Mass
Calculate m/z
268.037175
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Coumestan flavonoids [PK1209]

Biological Context

Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol) binds the estrogen receptors ERα (IC50 = 11 nM) and ERβ (IC50 = 2 nM) and can induce ER-dependent gene expression in isolated cells.1,2 Coumestrol is also a weak antagonist of pregnane X receptor (IC50 = 12 μM) as well as a potential inverse agonist of the constitutive androstane receptor (EC50 = 30 μM).3

This information has been provided by Cayman Chemical

References

1. Wang, H., Li, H., Moore, L.B., et al. The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor. Mol. Endocrinol. 22(4), 838-857 (2008).
2. Hopert, A.C., Beyer, A., Frank, K., et al. Characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. Environ. Health Perspect. 106(9), 581-586 (1998).
3. Chen, H.Y., Dykstra, K.D., Birzin, E.T., et al. Estrogen receptor ligands. Part 1: The discovery of flavanoids with subtype selectivity. Bioorg. Med. Chem. Lett. 14(6), 1417-1421 (2004).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
ZZIALNLLNHEQPJ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
SMILES (Click to copy)
C1(O)=CC2OC(=O)C3C4C=CC(O)=CC=4OC=3C=2C=C1

Other Databases

Wikipedia
Coumestrol
KEGG ID
C10205
HMDB ID
HMDB0002326
CHEBI ID
3908
METABOLOMICS ID
FLIE1ANS0001
PubChem CID
5281707
Cayman ID
11730
PDB ID
CUE
GuidePharm ID
12437

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 4
Aromatic Rings 4
Rotatable Bonds 0
Van der Waals Molecular Volume 197.85
Topological Polar Surface Area 83.81
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 4.00
Molar Refractivity 73.20

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Updated at
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