Showing Compound Coumestrol (FDB011663)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:45 UTC

Update date

2019-11-26 03:05:13 UTC

Primary ID

FDB011663

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Coumestrol

Description

Isolated 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 Number

479-13-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,9-Dihydroxycoumestan	ChEBI
Chrysanthin	ChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one	HMDB
Coumestrol	HMDB
Cumoesterol	HMDB
3,9-Dihydroxy-6-oxopterocarpen (obsol.)	db_source
3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one	biospider
3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9CI	db_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-Dihydroxycoumestan	biospider
7,12-Dihydroxycoumestan (obsol.)	db_source
Cumoestrol	biospider
Cumostrol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
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

Chemical Formula

C15H8O5

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

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

Isomeric SMILES

OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

Average Molecular Weight

268.224

Monoisotopic Molecular Weight

268.037173358

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.

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 67.17%; H 3.01%; O 29.82%	DFC
Melting Point	Mp 385°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	385 () (NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Coumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00rf-0090000000-24d398554cf83008a0b2	Spectrum
Predicted GC-MS	Coumestrol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3029000000-09e31fd7995c1524643c	Spectrum
Predicted GC-MS	Coumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-3b007f8a59433c8c8102	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-3b007f8a59433c8c8102	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-5a91822fb14572c010a0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0290000000-75cc1c58769101835d99	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0290000000-75cc1c58769101835d99	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-2a1a393fb92c1f28256e	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-606e78910a0367fb9798	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-5a91822fb14572c010a0	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014i-0290000000-75cc1c58769101835d99	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0090000000-895c91406544dc79d34d	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0904-3940000000-5bc2aef444fc6910fc19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0090000000-9fa59481d26b0a93d7c8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-2a1a393fb92c1f28256e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-606e78910a0367fb9798	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-5a91822fb14572c010a0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0290000000-75cc1c58769101835d99	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-121d9805507777b81a75	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-b99e1506236f0fb0601d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1490000000-9ba6d9042addda981b5b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-a481cda3a4b436df23dd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-3606deabc4ddf6ecce16	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0390000000-71b617f0a4545c7f72cc	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

399

DrugBank ID

Not Available

HMDB ID

HMDB02326

CRC / DFC (Dictionary of Food Compounds) ID

GXS80-A:GXS80-A

EAFUS ID

Not Available

Dr. Duke ID

COUMESTROL

BIGG ID

Not Available

KNApSAcK ID

C00002514

HET ID

CUE

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Coumestrol

Phenol-Explorer Metabolite ID

399

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti lipedemic			DUKE
anti microbial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti osteoporotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypocholesterolemic			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
nematistat			DUKE
peroxidase inhibitor	23924	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
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE
utero trophic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	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

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not 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.