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
Synonyms
SynonymSource
3,9-DihydroxycoumestanChEBI
ChrysanthinChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-oneHMDB
CoumestrolHMDB
CumoesterolHMDB
3,9-Dihydroxy-6-oxopterocarpen (obsol.)db_source
3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-onebiospider
3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9CIdb_source
6',7-Dihydroxybenzofuro[3',2',3,4]coumarin (obsol.)db_source
6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-biospider
6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-biospider
7,12-Dihydroxycoumestanbiospider
7,12-Dihydroxycoumestan (obsol.)db_source
Cumoestrolbiospider
Cumostroldb_source
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
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 lipedemicAn agent that reduces lipid levels in the blood, playing a crucial role in managing hyperlipidemia. Therapeutically, it helps prevent cardiovascular diseases by lowering cholesterol and triglyceride levels, making it a key treatment for conditions like atherosclerosis and hypertriglyceridemia.DUKE
Anti microbial33281 An agent that inhibits the growth of microorganisms, such as bacteria, viruses, and fungi, playing a crucial role in preventing infections. Therapeutically, it is used to treat various infectious diseases, with key medical applications including wound care, respiratory infections, and gastrointestinal infections, ultimately reducing the risk of infection and promoting healing.DUKE
Anti osteoporotic52217 An agent that prevents or treats osteoporosis by promoting bone density, reducing bone resorption, and increasing calcium absorption, commonly used in managing osteoporosis, osteopenia, and preventing fractures.DUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
NematistatAn agent that disorients, paralyzes, or confuses nematodes, preventing root infestation, with potential therapeutic applications in agriculture and key medical uses in managing parasitic nematode infections.DUKE
Peroxidase inhibitor23924 An agent that blocks the activity of peroxidase enzymes, reducing oxidative stress and inflammation. Therapeutically, it has applications in managing conditions like cancer, neurodegenerative diseases, and cardiovascular disorders, where oxidative damage plays a key role.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Phytoalexin26115 A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.DUKE
Utero trophic52217 A hormone that stimulates uterine growth and development, playing a crucial role in pregnancy. Therapeutically, it's used to support embryonic implantation and fetal development, with key medical applications in infertility treatments, such as in vitro fertilization (IVF) and recurrent miscarriage prevention.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.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.