ChemFOnt: Showing chemical card for Vanillic acid glucuronide (CFc000220825)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:13 UTC

Chemfont ID

CFc000220825

Molecule Identification

Common Name

Vanillic acid glucuronide

Definition

Vanillic acid glucuronide belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Based on a literature review a significant number of articles have been published on Vanillic acid glucuronide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vanillate glucuronide	Generator
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)oxane-2-carboxylate	HMDB

Chemical Formula

C₁₄H₁₆O₁₀

Average Molecular Weight

344.272

Monoisotopic Molecular Weight

344.074346715

IUPAC Name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)oxane-2-carboxylic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C14H16O10/c1-22-7-4-5(2-3-6(7)15)13(21)24-14-10(18)8(16)9(17)11(23-14)12(19)20/h2-4,8-11,14-18H,1H3,(H,19,20)/t8-,9-,10+,11-,14?/m0/s1

InChI Key

BSTDQIXKAVCPLC-JLERCCTOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240572)

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0240572)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0240572)

Tea

Tea products (HMDB: HMDB0240572)

Fat and oil

Olive oil (HMDB: HMDB0240572)

Fruit

Fruits (HMDB: HMDB0240572)

Vegetable

Vegetables (HMDB: HMDB0240572)

Legumes (HMDB: HMDB0240572)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0240572)

Nut

Nuts (HMDB: HMDB0240572)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0240572)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	13.3 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.58	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.77	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.06 m³·mol⁻¹	ChemAxon
Polarizability	31.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240572

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093771

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

122402642

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Vanillic acid glucuronide (CFc000220825)

MOL for CFc000220825 (Vanillic acid glucuronide)

3D MOL for CFc000220825 (Vanillic acid glucuronide)

3D SDF for CFc000220825 (Vanillic acid glucuronide)

3D-SDF for CFc000220825 (Vanillic acid glucuronide)

PDB for CFc000220825 (Vanillic acid glucuronide)

3D PDB for CFc000220825 (Vanillic acid glucuronide)

SMILES for CFc000220825 (Vanillic acid glucuronide)

INCHI for CFc000220825 (Vanillic acid glucuronide)

Structure for CFc000220825 (Vanillic acid glucuronide)

3D Structure for CFc000220825 (Vanillic acid glucuronide)