ChemFOnt: Showing chemical card for Protocatechuic acid 4-O-sulfate (CFc000220645)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:53 UTC

Chemfont ID

CFc000220645

Molecule Identification

Common Name

Protocatechuic acid 4-O-sulfate

Definition

Protocatechuic acid sulfate, also known as 3,4-DHBA sulfate, is an endogenous phenolic acid found to be elevated in mice urine after rye-bran supplemented diets which makes this compound a potential urinary biomarker of whole grain intake (PMID: 25944556 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Protocatechuate 4-O-sulfate	Generator
Protocatechuate 4-O-sulphate	Generator
Protocatechuic acid 4-O-sulfuric acid	Generator
Protocatechuic acid 4-O-sulphuric acid	Generator
3-Hydroxy-sulfonyloxybenzoic acid	HMDB
3-HSOB	HMDB
3-Hydroxy-4-(sulfooxy)benzoic acid	HMDB
Protocatechuic acid sulfate	HMDB
Protocatechuic acid sulphate	HMDB
3,4-DHBA sulfate	HMDB
3,4-DHBA sulphate	HMDB

Chemical Formula

C₇H₆O₇S

Average Molecular Weight

234.18

Monoisotopic Molecular Weight

233.983423707

IUPAC Name

3-hydroxy-4-(sulfooxy)benzoic acid

Traditional Name

3-hydroxy-4-(sulfooxy)benzoic acid

CAS Registry Number

76496-12-3

SMILES

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

InChI Identifier

InChI=1S/C7H6O7S/c8-5-3-4(7(9)10)1-2-6(5)14-15(11,12)13/h1-3,8H,(H,9,10)(H,11,12,13)

InChI Key

NGQYUDIZIPNWJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

Alternative Parents

Substituents

Phenylsulfate
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240382)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.04 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	1.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.27 m³·mol⁻¹	ChemAxon
Polarizability	19.1 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

HMDB0240382

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031321

KNApSAcK ID

Not Available

Chemspider ID

169832

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 Protocatechuic acid 4-O-sulfate (CFc000220645)

MOL for CFc000220645 (Protocatechuic acid 4-O-sulfate)

3D MOL for CFc000220645 (Protocatechuic acid 4-O-sulfate)

3D SDF for CFc000220645 (Protocatechuic acid 4-O-sulfate)

3D-SDF for CFc000220645 (Protocatechuic acid 4-O-sulfate)

PDB for CFc000220645 (Protocatechuic acid 4-O-sulfate)

3D PDB for CFc000220645 (Protocatechuic acid 4-O-sulfate)

SMILES for CFc000220645 (Protocatechuic acid 4-O-sulfate)

INCHI for CFc000220645 (Protocatechuic acid 4-O-sulfate)

Structure for CFc000220645 (Protocatechuic acid 4-O-sulfate)

3D Structure for CFc000220645 (Protocatechuic acid 4-O-sulfate)