Coumestrol (CHEM016530)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:08 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016530
Identification
Common NameCoumestrol
ClassSmall Molecule
DescriptionIsolated from Medicago subspecies, Glycine max (soybean), Pisum sativum (pea), Spinacia oleracea (spinach), Brassica oleracea (cabbage), Dolichos biflorus (papadi), Melilotus alba (white melilot), Phaseolus subspecies (inc. lima beans, pinto beans) and Vigna unguiculata (all Leguminosae). Potential nutriceutical Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica.; Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. The chemical shape of coumestrol orients its two hydroxy groups in the same position as the two hydroxy groups in estradiol, allowing it to inhibit the activity of aromatase and hydroxysteroid dehydrogenase. These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.; Coumestrol, a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus.). (PMID: 10888516); Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells. (PMID: 8315272). Coumestrol is found in many foods, some of which are green bean, miso, other soy product, and fruits.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,9-DihydroxycoumestanChEBI
ChrysanthinChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-oneHMDB
CoumestrolHMDB
CumoesterolHMDB
Chemical FormulaC15H8O5
Average Molecular Mass268.224 g/mol
Monoisotopic Mass268.037 g/mol
CAS Registry Number479-13-0
IUPAC Name5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Namecoumestrol
SMILESOC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2
InChI IdentifierInChI=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
InChI KeyZZIALNLLNHEQPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP2.43ALOGPS
logP2.4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.62 m³·mol⁻¹ChemAxon
Polarizability26.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rf-0090000000-24d398554cf83008a0b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3029000000-09e31fd7995c1524643cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d99Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0290000000-75cc1c58769101835d99Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8baSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-2a1a393fb92c1f28256eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-606e78910a0367fb9798Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d99Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-895c91406544dc79d34dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0904-3940000000-5bc2aef444fc6910fc19Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-9fa59481d26b0a93d7c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-2a1a393fb92c1f28256eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-606e78910a0367fb9798Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-5a91822fb14572c010a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0290000000-75cc1c58769101835d99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0960010000-fe04b8935dfef822b8baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-121d9805507777b81a75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-b99e1506236f0fb0601dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1490000000-9ba6d9042addda981b5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a481cda3a4b436df23ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-3606deabc4ddf6ecce16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0390000000-71b617f0a4545c7f72ccSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002326
FooDB IDFDB011663
Phenol Explorer ID399
KNApSAcK IDC00002514
BiGG IDNot Available
BioCyc IDCPD-11779
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCoumestrol
Chemspider ID4445024
ChEBI ID3908
PubChem Compound ID5281707
Kegg Compound IDC10205
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kappe, Thomas; Brandner, Alexander. Simple synthesis of coumestrol. Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie (1974), 29(3-4), 292-3.
2. Boue SM, Carter CH, Ehrlich KC, Cleveland TE: Induction of the soybean phytoalexins coumestrol and glyceollin by Aspergillus. J Agric Food Chem. 2000 Jun;48(6):2167-72.
3. Miksicek RJ: In situ localization of the estrogen receptor in living cells with the fluorescent phytoestrogen coumestrol. J Histochem Cytochem. 1993 Jun;41(6):801-10.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22644850
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22694330
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22824334
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22926873
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23348407