ChemFOnt: Showing chemical card for 4'-O-Methylepicatechin 7-O-glucuronide (CFc000010435)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:52 UTC

Chemfont ID

CFc000010435

Molecule Identification

Common Name

4'-O-Methylepicatechin 7-O-glucuronide

Definition

4'-O-Methylepicatechin 7-O-glucuronide (4ME7G) 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. 4'-O-Methyl-(-)-epicatechin 7-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). (−)-Epicatechin is taken up by Caco-2 cells (i.e. intestinal epithelial cells) and intracellularly metabolized into many products including 4ME7G (PMID: 24717599 ). 4ME7G is a cocoa metabolite from gut microflora. It has been found in urine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₂H₂₄O₁₂

Average Molecular Weight

480.422

Monoisotopic Molecular Weight

480.126776213

IUPAC Name

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

CAS Registry Number

603133-93-3

SMILES

COC1=C(O)C=C(C=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/c1-31-14-3-2-8(4-12(14)24)19-13(25)7-10-11(23)5-9(6-15(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

CJPIUMOCTBARLM-ZRRVXMDUSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
Catechin
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Fatty acyl
Hydroxy acid
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0029183)

Organ

Liver (HMDB: HMDB0029183)
Kidney (HMDB: HMDB0029183)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0029183)

Source

Endogenous

Endogenous (HMDB: HMDB0029183)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.32 g/L	ALOGPS
logP	0.29	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	46.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029183

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101244288

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4'-O-Methylepicatechin 7-O-glucuronide (CFc000010435)

MOL for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

3D MOL for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

3D SDF for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

3D-SDF for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

PDB for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

3D PDB for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

SMILES for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

INCHI for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

Structure for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)

3D Structure for CFc000010435 (4'-O-Methylepicatechin 7-O-glucuronide)