ContaminantDB: 3'-Methylepicatechin 7-glucuronide

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

Record Information

Version

1.0

Creation Date

2016-05-27 01:33:28 UTC

Update Date

2016-11-09 01:22:29 UTC

Accession Number

CHEM041526

Identification

Common Name

3'-Methylepicatechin 7-glucuronide

Class

Small Molecule

Description

3'-O-Methylepicatechin 7-O-glucuronide (3ME7G) belongs to the class of organic compounds known as flavonoid-7-O-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. 3'-O-Methyl-(-)-epicatechin 7-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). (−)-Epicatechin is taken up by HUVECs (i.e. endothelial cells) and intracellularly metabolized into 3ME7G and 3'-O-methylepicatechin 7-O-sulfate (3ME7S) (PMID: 24717599). 3ME7G is a polyphenol metabolite detected in biological fluids (PMID: 20428313).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-6-{[(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
3'-O-Methyl-(-)-epicatechin 7-O-glucuronide	HMDB
3'-O-Methyl-(-)-epicatechin 7-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-O-beta-D-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-O-beta-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-O-β-D-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-O-β-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-beta-D-glucuronide	HMDB
3'-O-Methyl-(−)-epicatechin-7-β-D-glucuronide	HMDB
3'-O-Methylepicatechin 7-glucuronide	HMDB
3ME7g	HMDB
3’-O-methyl-(-)-epicatechin 7-O-glucuronide	HMDB
3’-O-methyl-(-)-epicatechin 7-glucuronide	HMDB
3’-O-methyl-(−)-epicatechin-7-O-β-D-glucuronide	HMDB
3’-O-methyl-(−)-epicatechin-7-O-β-glucuronide	HMDB
3’-O-methyl-(−)-epicatechin-7-β-D-glucuronide	HMDB
3’-O-methylepicatechin 7-O-glucuronide	HMDB
3’-O-methylepicatechin 7-glucuronide	HMDB
3'-O-Methylepicatechin 7-O-glucuronide	HMDB

Chemical Formula

C₂₂H₂₄O₁₂

Average Molecular Mass

480.419 g/mol

Monoisotopic Mass

480.127 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

SMILES

COC1=C(O)C=CC(=C1)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=C2

InChI Identifier

InChI=1S/C22H24O12/c1-31-15-4-8(2-3-11(15)23)19-13(25)7-10-12(24)5-9(6-14(10)33-19)32-22-18(28)16(26)17(27)20(34-22)21(29)30/h2-6,13,16-20,22-28H,7H2,1H3,(H,29,30)/t13-,16+,17+,18-,19-,20+,22-/m1/s1

InChI Key

MZJSKSYVZZIYPF-ZRRVXMDUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.28 g/L	ALOGPS
logP	0.27	ALOGPS
logP	-0.0068	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.49 m³·mol⁻¹	ChemAxon
Polarizability	45.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	splash10-08i0-9208500000-f5f41649d075569db92e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001i-4211129000-bd9c4db314a9c0963f7a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bu9-0366900000-77914a82faf07ed8d187	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0974100000-79314cb0f412b503e235	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0910000000-273e45aba39094771bee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fbi-1214900000-db478eb381df9f30ea48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uy0-3948700000-184343518b3023bb2c6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-4954000000-068d5d382e124958df6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0012900000-9d2a9b58bf6c8e308a20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bu9-0529500000-fae8c6ed29feb07c6d9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gwr-2729200000-ebc256e4a89a12695d2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0501900000-4e84bc02188ebacb5cd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-6659800000-856b22afbf3394a5009b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-5456900000-1b894f523caefebb5aa3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	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

HMDB0041659

FooDB ID

FDB029815

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

30777591

ChEBI ID

Not Available

PubChem Compound ID

101190386

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.

2. Rodriguez-Mateos A, Toro-Funes N, Cifuentes-Gomez T, Cortese-Krott M, Heiss C, Spencer JP: Uptake and metabolism of (-)-epicatechin in endothelial cells. Arch Biochem Biophys. 2014 Oct 1;559:17-23. doi: 10.1016/j.abb.2014.03.014. Epub 2014 Apr 6.

3'-Methylepicatechin 7-glucuronide (CHEM041526)

Structure for CHEM041526: 3'-Methylepicatechin 7-glucuronide