ChemFOnt: Showing chemical card for 3'-O-Methylepicatechin 7-O-glucuronide (CFc000022521)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:53 UTC

Chemfont ID

CFc000022521

Molecule Identification

Common Name

3'-O-Methylepicatechin 7-O-glucuronide

Definition

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 ).

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 Weight

480.4188

Monoisotopic Molecular Weight

480.126776232

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

CAS Registry Number

603133-94-4

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0041659)

Organ

Liver (HMDB: HMDB0041659)
Kidney (HMDB: HMDB0041659)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0041659)

Cellular substructure

Extracellular (HMDB: HMDB0041659)
Cytoplasm (HMDB: HMDB0041659)

Source

Endogenous

Endogenous (HMDB: HMDB0041659)

Plant

Plant (HMDB: HMDB0041659)

Exogenous

Food

Food (HMDB: HMDB0041659)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041659)

Tea

Tea products (HMDB: HMDB0041659)

Nut

Nuts (HMDB: HMDB0041659)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041659)

Fruit

Berries (HMDB: HMDB0041659)

Pome

Apple (HMDB: HMDB0041659)

Exogenous (HMDB: HMDB0041659)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0041659)

Physical Properties

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	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

HMDB0041659

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029815

KNApSAcK ID

Not Available

Chemspider ID

30777591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101190386

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3'-O-Methylepicatechin 7-O-glucuronide (CFc000022521)

MOL for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

3D MOL for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

3D SDF for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

3D-SDF for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

PDB for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

3D PDB for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

SMILES for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

INCHI for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

Structure for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)

3D Structure for CFc000022521 (3'-O-Methylepicatechin 7-O-glucuronide)