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Coumestrol (FDB011663)

Record Information
Version1.0
Creation date2010-04-08 22:09:45 UTC
Update date2019-11-26 03:05:13 UTC
Primary IDFDB011663
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCoumestrol
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.
CAS Number479-13-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H8O5
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
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
Isomeric SMILESOC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2
Average Molecular Weight268.224
Monoisotopic Molecular Weight268.037173358
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.17%; H 3.01%; O 29.82%DFC
Melting PointMp 385°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data385 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCoumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00rf-0090000000-24d398554cf83008a0b2Spectrum
Predicted GC-MSCoumestrol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3029000000-09e31fd7995c1524643cSpectrum
Predicted GC-MSCoumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-3b007f8a59433c8c81022017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-3b007f8a59433c8c81022017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a02017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d992017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0290000000-75cc1c58769101835d992017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8ba2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-2a1a393fb92c1f28256e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-606e78910a0367fb97982017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d992017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-895c91406544dc79d34d2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8ba2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0904-3940000000-5bc2aef444fc6910fc192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-9fa59481d26b0a93d7c82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-2a1a393fb92c1f28256e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-606e78910a0367fb97982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-5a91822fb14572c010a02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0290000000-75cc1c58769101835d992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0960010000-fe04b8935dfef822b8ba2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-121d9805507777b81a752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-b99e1506236f0fb0601d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1490000000-9ba6d9042addda981b5b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a481cda3a4b436df23dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-3606deabc4ddf6ecce162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0390000000-71b617f0a4545c7f72cc2016-08-03View Spectrum
NMRNot Available
ChemSpider ID4445024
ChEMBL IDCHEMBL30707
KEGG Compound IDC10205
Pubchem Compound ID5281707
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID399
DrugBank IDNot Available
HMDB IDHMDB02326
CRC / DFC (Dictionary of Food Compounds) IDGXS80-A:GXS80-A
EAFUS IDNot Available
Dr. Duke IDCOUMESTROL
BIGG IDNot Available
KNApSAcK IDC00002514
HET IDCUE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCoumestrol
Phenol-Explorer Metabolite ID399
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti lipedemicDUKE
anti microbial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti osteoporotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypocholesterolemicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
nematistatDUKE
peroxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
utero trophic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.