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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2020-02-26 21:24:03 UTC
Secondary Accession Numbers
  • HMDB02326
Metabolite Identification
Common NameCoumesterol
DescriptionCumoesterol (or 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 ).
Chemical FormulaC15H8O5
Average Molecular Weight268.224
Monoisotopic Molecular Weight268.037173358
IUPAC Name5,14-dihydroxy-8,17-dioxatetracyclo[²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Namecoumestrol
CAS Registry Number479-13-0
InChI Identifier
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
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
  • 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

Route of exposure:


Biological location:

Physical Properties
Experimental Properties
Melting Point385 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.28 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified0.0123 +/- 0.0123 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000160 +/- 0.000800 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.00480 +/- 0.0144 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0208 +/- 0.112 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0081 (0.0033-0.0120) umol/mmol creatinineAdult (>18 years old)Both
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 399 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID399
FooDB IDFDB011663
KNApSAcK IDC00002514
Chemspider ID4445024
KEGG Compound IDC10205
BioCyc IDCPD-11779
BiGG IDNot Available
Wikipedia LinkCoumestrol
METLIN IDNot Available
PubChem Compound5281707
PDB IDNot Available
ChEBI ID3908
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceKappe, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:10888516 ]
  2. 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. [PubMed:8315272 ]


General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
Uniprot ID:
Molecular weight:
Coumesterol → 3,4,5-trihydroxy-6-({5-hydroxy-9-oxo-8,17-dioxatetracyclo[²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl}oxy)oxane-2-carboxylic aciddetails
Coumesterol → 3,4,5-trihydroxy-6-({14-hydroxy-9-oxo-8,17-dioxatetracyclo[²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl}oxy)oxane-2-carboxylic aciddetails