ChemFOnt: Showing chemical card for Vanillic acid 4-O-sulfate (CFc000022649)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:03 UTC

Chemfont ID

CFc000022649

Molecule Identification

Common Name

Vanillic acid 4-O-sulfate

Definition

Vanillic acid 4-O-sulfate is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Vanillic acid 4-O-sulfate was found to be elevated in rat urine after whole rye consumption which makes this compound a potential urinary biomarker of whole grain intake (PMID: 26862900 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vanillate 4-O-sulfate	Generator
Vanillate 4-O-sulphate	Generator
Vanillic acid 4-O-sulfuric acid	Generator
Vanillic acid 4-O-sulphuric acid	Generator
Vanillate 4-sulfate	HMDB
Vanillate 4-sulphate	HMDB
Vanillic acid 4-sulfuric acid	HMDB
Vanillic acid 4-sulphuric acid	HMDB
3-Methoxy-4-(sulfooxy)benzoate	HMDB
3-Methoxy-4-(sulphooxy)benzoate	HMDB
3-Methoxy-4-(sulphooxy)benzoic acid	HMDB
3-Methoxy-4-(sulfooxy)benzoic acid	HMDB
Vanillic acid 4-sulfate	HMDB
Vanillic acid 4-sulphate	HMDB
Vanillic acid sulfate	HMDB
Vanillic acid sulphate	HMDB
Vanillic acid-4-O-sulfate	HMDB
Vanillic acid-4-O-sulphate	HMDB

Chemical Formula

C₈H₈O₇S

Average Molecular Weight

248.21

Monoisotopic Molecular Weight

247.9990733

IUPAC Name

3-methoxy-4-(sulfooxy)benzoic acid

Traditional Name

3-methoxy-4-(sulfooxy)benzoic acid

CAS Registry Number

71235-86-4

SMILES

COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C8H8O7S/c1-14-7-4-5(8(9)10)2-3-6(7)15-16(11,12)13/h2-4H,1H3,(H,9,10)(H,11,12,13)

InChI Key

TXRKUXPAEPOCIX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

Phenylsulfate
M-methoxybenzoic acid or derivatives
Arylsulfate
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
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 (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 22827565)

Cellular substructure

Extracellular (HMDB: HMDB0041788)
Cytoplasm (HMDB: HMDB0041788)

Source

Endogenous

Endogenous (HMDB: HMDB0041788)

Exogenous

Food

Food (HMDB: HMDB0041788)
Legumes (HMDB: HMDB0041788)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041788)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0041788)

Tea

Tea products (HMDB: HMDB0041788)

Fat and oil

Olive oil (HMDB: HMDB0041788)

Fruit

Fruits (HMDB: HMDB0041788)

Vegetable

Vegetables (HMDB: HMDB0041788)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0041788)

Nut

Nuts (HMDB: HMDB0041788)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041788)

Exogenous (HMDB: HMDB0041788)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041788)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.38 g/L	ALOGPS
logP	-0.77	ALOGPS
logP	0.69	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.75 m³·mol⁻¹	ChemAxon
Polarizability	21.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041788

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029964

KNApSAcK ID

Not Available

Chemspider ID

339308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

382946

PDB ID

Not Available

ChEBI ID

88847

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Vanillic acid 4-O-sulfate (CFc000022649)

MOL for CFc000022649 (Vanillic acid 4-O-sulfate)

3D MOL for CFc000022649 (Vanillic acid 4-O-sulfate)

3D SDF for CFc000022649 (Vanillic acid 4-O-sulfate)

3D-SDF for CFc000022649 (Vanillic acid 4-O-sulfate)

PDB for CFc000022649 (Vanillic acid 4-O-sulfate)

3D PDB for CFc000022649 (Vanillic acid 4-O-sulfate)

SMILES for CFc000022649 (Vanillic acid 4-O-sulfate)

INCHI for CFc000022649 (Vanillic acid 4-O-sulfate)

Structure for CFc000022649 (Vanillic acid 4-O-sulfate)

3D Structure for CFc000022649 (Vanillic acid 4-O-sulfate)