ContaminantDB: Coumestrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 23:58:03 UTC

Update Date

2016-11-09 01:18:31 UTC

Accession Number

CHEM027765

Identification

Common Name

Coumestrin

Class

Small Molecule

Description

Coumestrin is found in alfalfa. Coumestrin is a constituent of Glycine max (soybean).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Coumestrol 3-O-glucoside	HMDB

Chemical Formula

C₂₁H₁₈O₁₀

Average Molecular Mass

430.362 g/mol

Monoisotopic Mass

430.090 g/mol

CAS Registry Number

92631-72-6

IUPAC Name

14-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

14-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

SMILES

OCC1OC(OC2=CC3=C(C=C2)C2=C(C4=C(O2)C=C(O)C=C4)C(=O)O3)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H18O10/c22-7-14-16(24)17(25)18(26)21(31-14)28-9-2-4-11-13(6-9)30-20(27)15-10-3-1-8(23)5-12(10)29-19(11)15/h1-6,14,16-18,21-26H,7H2

InChI Key

JSKGNHCHUPJTOQ-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Phenolic glycoside
Angular furanocoumarin
Furanocoumarin
Hexose monosaccharide
Coumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Monosaccharide
Oxane
Furan
Heteroaromatic compound
Lactone
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.89 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.13	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.76 m³·mol⁻¹	ChemAxon
Polarizability	42.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-7945500000-182ed2c632990f55cd56	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001i-3614129000-39a8e8b68309a7c4df5b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-014i-0090100000-75afe0d832435101a4fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0159-0190300000-5b11ed640294173807c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0190700000-4cdf8ada18334110fa49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-cc2737e5e4bf7d81ba6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-2190000000-535746ee1c548e116b14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-1163900000-8457d3dfacb38bfeee03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1091100000-a3b6d561a86369ed9bc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-2090000000-b4da6018be59bd3def0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-0280900000-2d95c4ed94702ed7bac1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2091200000-3f423ed0c55aff2b60a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-0090000000-655e93d78954f9cc6f7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0061900000-edd58ead8e6ce041e188	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0191000000-039705b81e302dad4634	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9172100000-81001279babf3b114d17	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033587

FooDB ID

FDB011664

Phenol Explorer ID

Not Available

KNApSAcK ID

C00010191

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

182658

PubChem Compound ID

74977392

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Coumestrin (CHEM027765)

Structure for CHEM027765: Coumestrin