Showing Compound 9-O-Methylcoumestrol (FDB011665)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:46 UTC

Update date

2019-11-26 03:05:13 UTC

Primary ID

FDB011665

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

9-O-Methylcoumestrol

Description

9-O-Methylcoumestrol 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, 9-O-methylcoumestrol is considered to be a flavonoid. 9-O-Methylcoumestrol has been detected, but not quantified in, several different foods, such as chickpeas (Cicer arietinum), herbs and spices, green vegetables, pulses, and common peas (Pisum sativum). This could make 9-O-methylcoumestrol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 9-O-Methylcoumestrol.

CAS Number

1690-62-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Search:

Synonym	Source
12-O-Methylcoumestrol	HMDB
3-Hydroxy-9-methoxycoumestan	HMDB
4'-Methoxycoumestrol	HMDB
4'-O-Methylcoumestrol	HMDB
9-O-Methylcoumestrol	db_source
Methyl N-methylnipecotate	HMDB
Methyl n-methylnipecotate	biospider

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.85	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	28.55 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

C16H10O5

IUPAC name

5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

InChI Identifier

InChI=1S/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

InChI Key

HHEZPZWGHDOWCQ-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

Average Molecular Weight

282.2476

Monoisotopic Molecular Weight

282.05282343

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
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090019 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Fabaceae

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 68.09%; H 3.57%; O 28.34%	DFC
Melting Point	Mp 338-339°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	9-O-Methylcoumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f80-0190000000-94c11589b4285910e5d8	Spectrum
Predicted GC-MS	9-O-Methylcoumestrol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g5i-4779000000-921bc270bf36e4137802	Spectrum
Predicted GC-MS	9-O-Methylcoumestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-1ff7411520d6ff0f22e6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-dcbe2788c89b14ce9a8d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gdi-0090000000-7c3dc506068d21eb5b43	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-bf271b4239f9685356ef	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-76e8557afe95a6a46488	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1090000000-9989e1a4f1e55a6c4f62	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053v-0190000000-fece2d85dbb0fd2da10b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-60166d79143e3c19fb0f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-cab7882440e1204f1c6e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbi-0090000000-9531507e13c5ce98799b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4477838

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5319565

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33588

CRC / DFC (Dictionary of Food Compounds) ID

GXS80-A:GXS82-C

EAFUS ID

Not Available

Dr. Duke ID

9-O-METHYLCOUMESTROL

BIGG ID

Not Available

KNApSAcK ID

C00009757

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound 9-O-Methylcoumestrol (FDB011665)

Structure for FDB011665 (9-O-Methylcoumestrol)