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Record Information
Version	2.0
Creation Date	2012-07-30 14:54:41 -0600
Update Date	2015-06-03 17:20:43 -0600
Secondary Accession Numbers	ECMDB21138
Identification
Name:	2,3-Dihydroxybenzoylserine
Description	2,3-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa7e6bbec> Close
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.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Benzene and substituted derivatives
Sub Class	Benzoic acids and derivatives
Direct Parent	Hippuric acids
Alternative Parents	N-acyl-alpha amino acids Serine and derivatives Salicylamides Benzoyl derivatives Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Beta hydroxy acids and derivatives Vinylogous acids Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Primary alcohols
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 Framework	Aromatic homomonocyclic compounds
External Descriptors	L-serine derivative (CHEBI:17455 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.76 g/L ALOGPS logP 0.33 ALOGPS logP 0.09 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 2.98 ChemAxon pKa (Strongest Basic) -2 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 127.09 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 56.12 m³·mol⁻¹ ChemAxon Polarizability 22.06 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 peptides PW000760
KEGG Pathways:	Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00dl-0390000000-1c8bd41059bced330983 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-2920000000-bc9d7862d6e634ce299e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00n0-9500000000-dca0ea7939deb8a40bf0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-0490000000-5529ba05e060a66aa481 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0nvm-2940000000-7ab5cdf84a6c5cab4263 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0pbl-9500000000-4a04c984745c207267b5 View 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
Links
External Links:	Resource Link CHEBI ID 17455 HMDB ID Not Available Pubchem Compound ID 25244759 Kegg ID C04204 ChemSpider ID 133509 Wikipedia ID Not Available BioCyc ID N-23-DIHYDROXYBENZOYL-L-SERINE EcoCyc ID N-23-DIHYDROXYBENZOYL-L-SERINE Ligand Expo DBS

Enzymes