2,3-Dihydroxybenzoic acid (ECMDB24184) (M2MDB006301)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (5)XML
Proteins (5)
Record Information
Version2.0
Creation Date2015-09-08 17:49:57 -0600
Update Date2016-09-13 16:35:43 -0600
Secondary Accession Numbers
  • ECMDB24184
Identification
Name:2,3-Dihydroxybenzoic acid
Description2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3-Dihydroxybenzoate
Chemical Formula:
Weight:Average: Not Available
Monoisotopic: Not Available
InChI Key:Not Available
InChI:Not Available
CAS number:Not Available
IUPAC Name:2-carboxy-6-hydroxybenzen-1-olate
Traditional IUPAC Name:2-carboxy-6-hydroxybenzenolate
SMILES:Not Available
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Phenoxide
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility29.1 g/LALOGPS
logP0.53ALOGPS
logP1.67ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.83 m³·mol⁻¹ChemAxon
Polarizability13.39 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2,3-Dihydroxybenzoic acid + NADH + Hydrogen ion
6 Adenosine triphosphate + 3 L-Serine + 3 2,3-Dihydroxybenzoic acid + 3 L-Serine >6 Adenosine monophosphate + enterobactin +6 Pyrophosphate +3 Hydrogen ion
Adenosine triphosphate + 2,3-Dihydroxybenzoic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid
Adenosine triphosphate + 2,3-Dihydroxybenzoic acid <> (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate
2,3-Dihydroxybenzoic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate
SMPDB Pathways:
Biosynthesis of siderophore group nonribosomal peptidesPW000760 ThumbThumb?image type=greyscaleThumb?image type=simple
Enterobactin BiosynthesisPW002048 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID36654
HMDB IDNot Available
Pubchem Compound ID6950143
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia ID2,3-Dihydroxybenzoic acid
BioCyc IDNot Available

Enzymes

Protein Details
1. Isochorismatase
General function:
Involved in isochorismatase activity
Specific function:
Required for production of 2,3-DHB. Also serves as an aryl carrier protein and plays a role in enterobactin assembly
Gene Name:
entB
Uniprot ID:
P0ADI4
Molecular weight:
32554
Reactions
Isochorismate + H(2)O = 2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate.
Protein Details
2. Enterobactin synthase component E
General function:
Involved in catalytic activity
Specific function:
Activates the carboxylate group of 2,3-dihydroxy- benzoate (2,3-DHB), via ATP-dependent PPi exchange reactions, to the acyladenylate. Then, catalyzes the acylation of holo-entB with 2,3-DHB adenylate, preparing that molecule for amide bond formation with L-serine
Gene Name:
entE
Uniprot ID:
P10378
Molecular weight:
59112
Reactions
ATP + 2,3-dihydroxybenzoate = diphosphate + (2,3-dihydroxybenzoyl)adenylate.
(2,3-dihydroxybenzoyl)adenylate + holo-entB = adenosine 5'-monophosphate + acyl-holo-entB.
Protein Details
3. Enterobactin synthase component F
General function:
Involved in ligase activity
Specific function:
Activates the carboxylate group of L-serine via ATP- dependent PPi exchange reactions to the aminoacyladenylate, preparing that molecule for the final stages of enterobactin synthesis. Holo-entF acts as the catalyst for the formation of the three amide and three ester bonds present in the cyclic (2,3- dihydroxybenzoyl)serine trimer enterobactin, using seryladenylate and acyl-holo-entB (acylated with 2,3-dihydroxybenzoate by entE)
Gene Name:
entF
Uniprot ID:
P11454
Molecular weight:
141990
Reactions
ATP + L-serine = diphosphate + L-serine-adenylate.
Protein Details
4. 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
2,3-dihydro-2,3-dihydroxybenzoate + NAD(+) = 2,3-dihydroxybenzoate + NADH
Gene Name:
entA
Uniprot ID:
P15047
Molecular weight:
26250
Reactions
2,3-dihydro-2,3-dihydroxybenzoate + NAD(+) = 2,3-dihydroxybenzoate + NADH.
Protein Details
5. 4'-phosphopantetheinyl transferase entD
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the transfer of the 4'-phosphopantetheine moiety from coenzyme A to apo-domains of both entB (an ArCP domain) and entF (a PCP domain). Plays an essential role in the assembly of the enterobactin
Gene Name:
entD
Uniprot ID:
P19925
Molecular weight:
23604
Reactions
CoA + apo-EntB/F = adenosine 3',5'-bisphosphate + holo-EntB/F.