NP-MRD: Showing NP-Card for Coumestrol (NP0047674)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:03 UTC

Updated at

2025-02-11 15:46:26 UTC

NP-MRD ID

NP0047674

Natural Product DOI

https://doi.org/10.57994/0926

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coumestrol

Description

Coumesterol, also known as chrysanthin, 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. Thus, coumesterol is considered to be a flavonoid lipid molecule. Coumesterol (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 ). Coumesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Coumesterol is a bitter tasting compound. Outside of the human body, Coumesterol is found, on average, in the highest concentration within a few different foods, such as brussel sprouts, common pea, and soy beans and in a lower concentration in other soy products, miso, and tofus. Coumesterol has also been detected, but not quantified in, several different foods, such as lima beans, pulses, yellow wax beans, black-eyed pea, and sunflowers. This could make coumesterol a potential biomarker for the consumption of these foods. Such observations illustrate the potential for using Coumesterol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells (PMID: 8315272 ). Coumesterol 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. Coumestrol is found in Apis cerana, Bituminaria morisiana, Brassica oleracea , Campylotropis hirtella, Cullen corylifolium, Glycine canescens, Glycine clandestina, Glycine falcata, Glycine latifolia, Glycine tabacina, Glycine tomentella, Homo sapiens (Urine), Medicago arabica, Medicago sativa , Medicago spp., Medicago truncatula, Melilotus alba, Melilotus messanensis, Phaseolus spp., Pueraria candollei, Pueraria lobata , Pueraria mirifica , Pueraria montana, Pueraria montana var. lobata, Tephrosia purpurea, Trifolium fragiferum, Trifolium pratense , Trifolium repens , Trifolium subterraneum and Dolichos biflorus . Coumestrol was first documented in 1993 (PMID: 8315272). Coumesterol 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 (PMID: 10888516) (PMID: 22644850) (PMID: 22694330) (PMID: 22824334).

Structure

MOL SDF PDB SMILES InChI

Coumestrol
  Mrv1572001071617322D          

 20 23  0  0  0  0            999 V2000
    5.8101    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047674

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
ZZIALNLLNHEQPJ-UHFFFAOYSA-N

> <FORMULA>
C15H8O5

> <MOLECULAR_WEIGHT>
268.224

> <EXACT_MASS>
268.037173358

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
26.40531448424779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.3973213223333327

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111552628222421

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.110949661336945

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0531035874613637

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
69.6195

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coumestrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Coumestrol                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      10.846   2.182   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.372   2.147   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.179  -0.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.024  -1.805   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.406  -3.004   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.741   0.594   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   20                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   11                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
3,9-Dihydroxycoumestan	ChEBI
Chrysanthin	ChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one	HMDB
Coumestrol	HMDB
Cumoesterol	HMDB

Chemical Formula

C₁₅H₈O₅

Average Mass

268.2240 Da

Monoisotopic Mass

268.03717 Da

IUPAC Name

5,14-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 Name

coumestrol

CAS Registry Number

479-13-0

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 Key

ZZIALNLLNHEQPJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Bituminaria morisiana	Plant	KNApSAcK
Brassica oleracea	Plant	KNApSAcK
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Campylotropis hirtella	LOTUS Database	35616633
Cullen corylifolium	Plant	KNApSAcK
Glycine canescens	Plant	KNApSAcK
Glycine clandestina	Plant	KNApSAcK
Glycine falcata	Plant	KNApSAcK
Glycine latifolia	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycine tabacina	Plant	KNApSAcK
Glycine tomentella	Plant	KNApSAcK
Helianthus annuus L.	FooDB	PHENOL EXPLORER
Homo sapiens (Urine)	Animalia	KNApSAcK
Medicago arabica	Plant	KNApSAcK
Medicago sativa	Plant	KNApSAcK
Medicago spp.	Plant	KNApSAcK
Medicago truncatula	Plant	KNApSAcK
Melilotus alba	Plant	KNApSAcK
Melilotus messanensis	Plant	KNApSAcK
Phaseolus coccineus	FooDB	KNAPSACK
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus spp.	Plant	KNApSAcK
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pueraria candollei var. mirifica	LOTUS Database	35616633
Pueraria lobata	Plant	KNApSAcK
Pueraria mirifica	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Pueraria montana var. lobata	Plant	KNApSAcK
Punica granatum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tephrosia purpurea	LOTUS Database	35616633
Trifolium fragiferum	Plant	KNApSAcK
Trifolium pratense	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Trifolium subterraneum	Plant	KNApSAcK
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata	FooDB	KNAPSACK
Vigna unguiculata ssp. cylindrica	Plant	KNApSAcK
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:3908 )
delta-lactone (CHEBI:3908 )
coumestans (CHEBI:3908 )
Coumestan flavonoids (C10205 )
Coumestanes (C10205 )
Coumestan flavonoids (LMPK12090018 )
an isoflavone (CPD-11779 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.43	ALOGPS
logP	2.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.62 m³·mol⁻¹	ChemAxon
Polarizability	26.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002326

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Coumestrol

METLIN ID

Not Available

PubChem Compound

5281707

PDB ID

Not Available

ChEBI ID

3908

Good Scents ID

Not Available

References

General References

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. doi: 10.1021/jf9912809. [PubMed:10888516 ]
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. doi: 10.1177/41.6.8315272. [PubMed:8315272 ]
Jin SE, Son YK, Min BS, Jung HA, Choi JS: Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots. Arch Pharm Res. 2012 May;35(5):823-37. doi: 10.1007/s12272-012-0508-x. Epub 2012 May 29. [PubMed:22644850 ]
Ueda M, Horiguchi Y, Sugimoto M, Ikeda S, Kume S: Effects of coumestrol administration to maternal mice during pregnancy and lactation on renal Ca metabolism in neonatal mice. Anim Sci J. 2012 Jun;83(6):469-73. doi: 10.1111/j.1740-0929.2011.00977.x. Epub 2011 Dec 8. [PubMed:22694330 ]
Canal Castro C, Pagnussat AS, Orlandi L, Worm P, Moura N, Etgen AM, Alexandre Netto C: Coumestrol has neuroprotective effects before and after global cerebral ischemia in female rats. Brain Res. 2012 Sep 20;1474:82-90. doi: 10.1016/j.brainres.2012.07.025. Epub 2012 Jul 21. [PubMed:22824334 ]

Showing NP-Card for Coumestrol (NP0047674)

MOL for NP0047674 (Coumestrol)

3D MOL for NP0047674 (Coumestrol)

3D SDF for NP0047674 (Coumestrol)

3D-SDF for NP0047674 (Coumestrol)

PDB for NP0047674 (Coumestrol)

3D PDB for NP0047674 (Coumestrol)

SMILES for NP0047674 (Coumestrol)

INCHI for NP0047674 (Coumestrol)

Structure for NP0047674 (Coumestrol)

3D Structure for NP0047674 (Coumestrol)