MiMeDB: Showing metabocard for 3,4-dihydroxybenzoic acid (MMDBc0054247)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:01:23 UTC

Update Date

2022-09-01 02:28:00 UTC

Metabolite ID

MMDBc0054247

Metabolite Identification

Common Name

3,4-dihydroxybenzoic acid

Description

3,4-dihydroxybenzoate, also known as 4,5-dihydroxybenzoic acid, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). A dihydroxybenzoate having the two hydroxy groups located at the 3- and 4-positions.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,5-Dihydroxybenzoate	ChEBI
4,5-Dihydroxybenzoic acid	Generator
3,4-Dihydroxybenzoic acid	Generator

Molecular Formula

C₇H₅O₄

Average Mass

153.114

Monoisotopic Mass

153.019332221

IUPAC Name

3,4-dihydroxybenzoate

Traditional Name

protocatechuate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1O)C([O-])=O

InChI Identifier

InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)/p-1

InChI Key

YQUVCSBJEUQKSH-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Hydroxybenzoic acid
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Phenoxide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoate (CHEBI:36241 )
a catechol (3-4-DIHYDROXYBENZOATE )
an aromatic carboxylate (3-4-DIHYDROXYBENZOATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	28.8 g/L	ALOGPS
logP	0.65	ALOGPS
logP	1.02	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.11 m³·mol⁻¹	ChemAxon
Polarizability	13.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	11	Human ; Human subgingival plaque; Human supragingival plaque
Eukaryota/Fungi	Ascomycota	2
Bacteria	Firmicutes	4	Human ; Human feces

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

3-4-DIHYDROXYBENZOATE

BiGG ID

Not Available

Wikipedia Link

Protocatechuic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

36241

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Brunel F, Davison J: Cloning and sequencing of Pseudomonas genes encoding vanillate demethylase. J Bacteriol. 1988 Oct;170(10):4924-30. doi: 10.1128/jb.170.10.4924-4930.1988. [PubMed:3170489 ]
Michalover JL, Ribbons DW, Hughes H: 3-Hydroxybenzoate 4-hydroxylase from Pseudomonas testosteroni. Biochem Biophys Res Commun. 1973 Dec 10;55(3):888-96. doi: 10.1016/0006-291x(73)91227-8. [PubMed:4148586 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 3,4-dihydroxybenzoic acid (MMDBc0054247)

MOL for #<Metabolite:0x00007fdb2e68f2c0>

3D MOL for #<Metabolite:0x00007fdb2e68f2c0>

3D SDF for #<Metabolite:0x00007fdb2e68f2c0>

3D-SDF for #<Metabolite:0x00007fdb2e68f2c0>

PDB for #<Metabolite:0x00007fdb2e68f2c0>

3D PDB for #<Metabolite:0x00007fdb2e68f2c0>

SMILES for #<Metabolite:0x00007fdb2e68f2c0>

INCHI for #<Metabolite:0x00007fdb2e68f2c0>

Structure for #<Metabolite:0x00007fdb2e68f2c0>

3D Structure for #<Metabolite:0x00007fdb2e68f2c0>