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2,3-Dihydro-2,3-dihydroxybenzoic acid (M2MDB000587)

Record Information
Version2.0
Creation Date2012-05-31 14:03:45 -0600
Update Date2015-10-15 16:14:25 -0600
Secondary Accession Numbers
  • ECMDB04055
Identification
Name:2,3-Dihydro-2,3-dihydroxybenzoic acid
Description2,3-dihydro-2,3-dihydroxybenzoate is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 2,3-Dihydro-2,3-dihydroxybenzoate
  • 2,3-Dihydroxy-2,3-dihydrobenzoate
  • 2,3-Dihydroxy-2,3-dihydrobenzoic acid
  • Dihydro-dioh-benzoate
  • Dihydro-dioh-benzoic acid
Chemical Formula:C7H8O4
Weight:Average: 156.136
Monoisotopic: 156.042258744
InChI Key:INCSWYKICIYAHB-UHFFFAOYSA-N
InChI:InChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11)
CAS number:Not Available
IUPAC Name:5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate
Traditional IUPAC Name:5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate
SMILES:OC1C=CC=C(C1O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility261 g/LALOGPS
logP-0.29ALOGPS
logP-0.77ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.4 m³·mol⁻¹ChemAxon
Polarizability13.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD + 2,3-Dihydro-2,3-dihydroxybenzoic acid <> 2-Pyrocatechuic acid + Hydrogen ion + NADH
SMPDB Pathways:
Biosynthesis of siderophore group nonribosomal peptidesPW000760 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-f22f9ce9487ab9f40548View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-1900000000-21d4dc061986f186f086View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tg-9200000000-ae80b1567903ebfe8e1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-2693ca6245ee38bd85f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-2ad93a6edd5619a4cb79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0cdr-9300000000-9fa5140e2a459ae72aa6View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15941
HMDB IDNot Available
Pubchem Compound ID23615184
Kegg IDC04171
ChemSpider ID19951064
Wikipedia IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE
EcoCyc IDDIHYDRO-DIOH-BENZOATE

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. 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.