2,3-Dihydroxybenzoylserine (ECMDB21138) (M2MDB001547)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-07-30 14:54:41 -0600
Update Date2015-06-03 17:20:43 -0600
Secondary Accession Numbers
  • ECMDB21138
Identification
Name:2,3-Dihydroxybenzoylserine
Description2,3-dihydroxybenzoylserine is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 2,3-dihydroxybenzoylserine is invovled in Enterobactin degradation. It is a product of the enzyme 2,3-dihydroxybenzoate-serine ligase (EC 6.3.2.14) is an enzyme that catalyzes the chemical reaction ATP + 2,3-dihydroxybenzoate + L-serine ightleftharpoons products of ATP breakdown + N-(2,3-dihydroxybenzoyl)-L-serine. (PMID 4966114).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3-Dihydroxy-N-benzoyl-L-serine
  • 2,3-dihydroxybenzoylserine
  • 2,3DHBSer
  • 2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoate
  • 2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoic acid
  • N-(2,3-Dihydroxybenzoyl)-L-serine
Chemical Formula:C10H11NO6
Weight:Average: 241.1974
Monoisotopic: 241.058637089
InChI Key:VDTYHTVHFIIEIL-LURJTMIESA-N
InChI:InChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1
CAS number:127658-43-9
IUPAC Name:(2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid
Traditional IUPAC Name:2,3,-dihydroxybenzoylserine
SMILES:[H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Salicylamide
  • Salicylic acid or derivatives
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Beta-hydroxy acid
  • Hydroxy acid
  • Vinylogous acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility5.76 g/LALOGPS
logP0.33ALOGPS
logP0.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.12 m³·mol⁻¹ChemAxon
Polarizability22.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Enterochelin + 3 Water >3 2,3-Dihydroxybenzoylserine +3 Hydrogen ion
Ferric enterobactin + 3 Water >3 2,3-Dihydroxybenzoylserine + Fe3+ +3 Hydrogen ion
Enterochelin + Water > Hydrogen ion + 2,3-Dihydroxybenzoylserine
(2,3-dihydroxybenzoylserine)<sub>3</sub> + Water 2,3-Dihydroxybenzoylserine
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:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0390000000-1c8bd41059bced330983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2920000000-bc9d7862d6e634ce299eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-9500000000-dca0ea7939deb8a40bf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-5529ba05e060a66aa481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nvm-2940000000-7ab5cdf84a6c5cab4263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbl-9500000000-4a04c984745c207267b5View in MoNA
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17455
HMDB IDNot Available
Pubchem Compound ID25244759
Kegg IDC04204
ChemSpider ID133509
Wikipedia IDNot Available
BioCyc IDN-23-DIHYDROXYBENZOYL-L-SERINE
EcoCyc IDN-23-DIHYDROXYBENZOYL-L-SERINE
Ligand ExpoDBS

Enzymes

Protein Details
1. Enterochelin esterase
General function:
Involved in iron ion binding
Specific function:
Upon internalization, ferric enterobactin is processed via an exquisitely specific pathway that is dependent on FES activity, making iron available for metabolic use
Gene Name:
fes
Uniprot ID:
P13039
Molecular weight:
42569