Showing chemical card for Vanillic acid 4-beta-D-glucoside (CFc000281985)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:54 UTC

Chemfont ID

CFc000281985

Molecule Identification

Common Name

Vanillic acid 4-beta-D-glucoside

Definition

Vanillic acid 4-beta-d-glucoside, also known as vanillate 4-beta-D-glucoside, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins 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) 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. Vanillic acid 4-beta-d-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Vanillic acid 4-beta-d-glucoside can be found in a number of food items such as sweet marjoram, orange bell pepper, yellow bell pepper, and pepper (c. annuum), which makes vanillic acid 4-beta-d-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

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INCHI for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)/t9-,10-,11+,12-,14-/m1/s1

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Structure for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

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3D Structure for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

Synonyms

Value	Source
3-Methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
Vanillate 4-b-D-glucoside	Generator
Vanillate 4-beta-D-glucoside	Generator
Vanillate 4-β-D-glucoside	Generator
Vanillic acid 4-b-D-glucoside	Generator
Vanillic acid 4-β-D-glucoside	Generator
4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid	PhytoBank
4-(β-D-Glucopyranosyloxy)-3-methoxybenzoic acid	PhytoBank
4-O-beta-D-Glucopyranosylvanillc acid	PhytoBank
4-O-β-D-Glucopyranosylvanillc acid	PhytoBank
Vanillic acid 4-O-beta-D-glucopyranoside	PhytoBank
Vanillic acid 4-O-β-D-glucopyranoside	PhytoBank
Vanillic acid 4-beta-D-glucoside	PhytoBank
Vanillic acid glucoside	PhytoBank
Vanillic acid beta-glucoside	PhytoBank
Vanillic acid β-glucoside	PhytoBank
Vanillic acid-4-O-glucopyranoside	PhytoBank

Chemical Formula

C₁₄H₁₈O₉

Average Molecular Weight

330.289

Monoisotopic Molecular Weight

330.09508216

IUPAC Name

3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Traditional Name

3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

CAS Registry Number

None

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C14H18O9/c1-21-8-4-6(13(19)20)2-3-7(8)22-14-12(18)11(17)10(16)9(5-15)23-14/h2-4,9-12,14-18H,5H2,1H3,(H,19,20)/t9-,10-,11+,12-,14-/m1/s1

InChI Key

JYFOSWJYZIVJPO-YGEZULPYSA-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

Phenolic glycosides
Hexoses
O-glycosyl compounds
M-methoxybenzoic acids and derivatives
Benzoic acids
Anisoles
Phenoxy compounds
Benzoyl derivatives
Methoxybenzenes
Sugar acids and derivatives
Alkyl aryl ethers
Oxanes
Secondary alcohols
Acetals
Polyols
Oxacyclic compounds
Monocarboxylic acids and derivatives
Carboxylic acids
Primary alcohols
Organic oxides
Hydrocarbon derivatives

Substituents

Hydrolyzable tannin
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Alkyl aryl ether
Sugar acid
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tannin (CHEBI:68950 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302469)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herb

Sweet basil (FooDB: FOOD00119)
Sweet marjoram (FooDB: FOOD00122)
Rosemary (FooDB: FOOD00159)
Common thyme (FooDB: FOOD00183)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-0.97	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.9 m³·mol⁻¹	ChemAxon
Polarizability	31.2 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

HMDB0302469

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004688

KNApSAcK ID

Not Available

Chemspider ID

10290220

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Vanillic acid 4-beta-D-glucoside (CFc000281985)

MOL for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

3D MOL for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

3D SDF for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

3D-SDF for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

PDB for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

3D PDB for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

SMILES for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

INCHI for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

Structure for CFc000281985 (Vanillic acid 4-beta-D-glucoside)

3D Structure for CFc000281985 (Vanillic acid 4-beta-D-glucoside)