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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2019-01-11 19:16:57 UTC
HMDB IDHMDB0002326
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 ).
Structure
Data?1547234217
Synonyms
ValueSource
3,9-DihydroxycoumestanChEBI
ChrysanthinChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-oneHMDB
CoumestrolHMDB
CumoesterolHMDB
Chemical FormulaC15H8O5
Average Molecular Weight268.224
Monoisotopic Molecular Weight268.037173358
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
CAS Registry Number479-13-0
SMILES
OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2
InChI Identifier
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point385 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rf-0090000000-24d398554cf83008a0b2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3029000000-09e31fd7995c1524643cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0290000000-75cc1c58769101835d99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8baJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-2a1a393fb92c1f28256eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-606e78910a0367fb9798JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-5a91822fb14572c010a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0290000000-75cc1c58769101835d99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-895c91406544dc79d34dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0159-0960010000-fe04b8935dfef822b8baJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0904-3940000000-5bc2aef444fc6910fc19JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-9fa59481d26b0a93d7c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-2a1a393fb92c1f28256eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-606e78910a0367fb9798JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-5a91822fb14572c010a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0290000000-75cc1c58769101835d99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0960010000-fe04b8935dfef822b8baJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-121d9805507777b81a75JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-b99e1506236f0fb0601dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1490000000-9ba6d9042addda981b5bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a481cda3a4b436df23ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-3606deabc4ddf6ecce16JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0390000000-71b617f0a4545c7f72ccJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Normal
details
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
FoodDB 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
References
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 ]

Enzymes

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:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Coumesterol → 3,4,5-trihydroxy-6-({5-hydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]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[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl}oxy)oxane-2-carboxylic aciddetails