(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate (ECMDB20009) (M2MDB000858)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-05-31 14:22:38 -0600
Update Date2015-06-03 17:19:07 -0600
Secondary Accession Numbers
  • ECMDB20009
Identification
Name:(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate
Description(2S,3S)-2,3-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. It is involved in siderophore biosynthesis and enterobactin biosynthesis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoic acid
  • 2,3-Dihydro-2,3-dihydroxybenzoate
  • 2,3-Dihydro-2,3-dihydroxybenzoic acid
  • 2,3-Dihydroxy-2,3-dihydrobenzoate
  • 2,3-Dihydroxy-2,3-dihydrobenzoic acid
  • 5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylate
  • 5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylic acid
  • Dihydro-dioh-benzoate
  • Dihydro-dioh-benzoic acid
Chemical Formula:C7H8O4
Weight:Average: 156.136
Monoisotopic: 156.042258744
InChI Key:INCSWYKICIYAHB-WDSKDSINSA-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)/t5-,6-/m0/s1
CAS number:Not Available
IUPAC Name:(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid
Traditional IUPAC Name:(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid
SMILES:[H][C@]1(O)C=CC=C(C(O)=O)[C@]1([H])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
  • 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 Solubility92 g/LALOGPS
logP-0.33ALOGPS
logP-0.77ChemAxon
logS-0.23ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.56 m³·mol⁻¹ChemAxon
Polarizability14.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acid
(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD + 2,3-Dihydro-2,3-dihydroxybenzoic acid <> 2-Pyrocatechuic acid + Hydrogen ion + NADH
(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD <> 2-Pyrocatechuic acid + NADH + Hydrogen ion
NAD + (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate > Hydrogen ion + NADH + 2-Pyrocatechuic acid
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-d78c464be73680d74a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-55e0ad87d52424ba6356View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-025aa9020427079f7be2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0900000000-7f4188bec77a57b8b2eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2900000000-87f3d73fb0944c40d8e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9400000000-19b6ca0c7ff67902fa72View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 ID3
Kegg IDC04171
ChemSpider ID8139753
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.