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Record Information
Version2.0
Created at2021-01-06 06:46:53 UTC
Updated at2021-07-15 17:36:31 UTC
NP-MRD IDNP0021500
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3-Dihydroxy-N-benzoylserine
Provided ByNPAtlasNPAtlas Logo
DescriptionN-(2,3-dihydroxybenzoyl)serine, also known as 2,3-DHBS, 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. 2,3-Dihydroxy-N-benzoylserine is found in Escherichia coli. 2,3-Dihydroxy-N-benzoylserine was first documented in 2007 (PMID: 17973380). Based on a literature review a small amount of articles have been published on N-(2,3-dihydroxybenzoyl)serine (PMID: 30086222).
Structure
Data?1624506852
Synonyms
ValueSource
2,3-DHBSChEBI
2,3-Dihydroxy-N-benzoylserineChEBI
2,3-DihydroxybenzoylserineChEBI
2-(2,3-Dihydroxybenzamido)-3-hydroxypropanoic acidChEBI
2-[(2,3-Dihydroxybenzoyl)amino]-3-hydroxypropanoic acidChEBI
2-[(2,3-Dihydroxyphenyl)formamido]-3-hydroxypropanoic acidChEBI
2-(2,3-Dihydroxybenzamido)-3-hydroxypropanoateGenerator
2-[(2,3-Dihydroxybenzoyl)amino]-3-hydroxypropanoateGenerator
2-[(2,3-Dihydroxyphenyl)formamido]-3-hydroxypropanoateGenerator
Chemical FormulaC10H11NO6
Average Mass241.1990 Da
Monoisotopic Mass241.05864 Da
IUPAC Name(2R)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid
Traditional Name2,3,-dihydroxybenzoylserine
CAS Registry NumberNot Available
SMILES
OCC(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=O
InChI Identifier
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)
InChI KeyVDTYHTVHFIIEIL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Escherichia coliNPAtlas
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 DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability22.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA009062
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID570809
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound656417
PDB IDNot Available
ChEBI ID143101
Good Scents IDNot Available
References
General References
  1. Perraud Q, Moynie L, Gasser V, Munier M, Godet J, Hoegy F, Mely Y, Mislin GLA, Naismith JH, Schalk IJ: A Key Role for the Periplasmic PfeE Esterase in Iron Acquisition via the Siderophore Enterobactin in Pseudomonas aeruginosa. ACS Chem Biol. 2018 Sep 21;13(9):2603-2614. doi: 10.1021/acschembio.8b00543. Epub 2018 Aug 22. [PubMed:30086222 ]
  2. Nolan EM, Fischbach MA, Koglin A, Walsh CT: Biosynthetic tailoring of microcin E492m: post-translational modification affords an antibacterial siderophore-peptide conjugate. J Am Chem Soc. 2007 Nov 21;129(46):14336-47. doi: 10.1021/ja074650f. Epub 2007 Oct 31. [PubMed:17973380 ]