Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120185
Identification
Name: N-formyl-L-glutamate
Description:A doubly-charged N-acyl-L-α-amino acid anion resulting from deprotonation of both carboxy groups of N-formyl-L-glutamic acid.
Structure
Thumb
Synonyms:
  • (2S)-2-(formylamino)pentanedioate
  • N-formyl-L-glutamate
Chemical Formula: C6H7NO5
Average Molecular Weight: 173.125
Monoisotopic Molecular Weight: 175.04807
InChI Key: ADZLWSMFHHHOBV-BYPYZUCNSA-L
InChI:InChI=1S/C6H9NO5/c8-3-7-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/p-2/t4-/m0/s1
CAS number: 1681-96-5
IUPAC Name:(2S)-2-formamidopentanedioate
Traditional IUPAC Name: N-formyl-L-glutamic acid
SMILES:C(=O)NC(CCC(=O)[O-])C(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Glutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-formyl-alpha-amino acid
  • N-formyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.5 mg/mLALOGPS
logP-0.86ALOGPS
logP-1.2ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.24 m3·mol-1ChemAxon
Polarizability15.42 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra: Not Available
References
References:
  • Martí-Arbona R, Xu C, Steele S, Weeks A, Kuty GF, Seibert CM, Raushel FM (2006)Annotating enzymes of unknown function: N-formimino-L-glutamate deiminase is a member of the amidohydrolase superfamily. Biochemistry 45, Pubmed: 16475788
  • Coote JG, Hassall H (1973)The degradation of L-histidine, imidazolyl-L-lactate and imidazolylpropionate by Pseudomonas testosteroni. The Biochemical journal 132, Pubmed: 4146796
  • Haas D, Leisinger T (1975)N-acetylglutamate 5-phosphotransferase of Pseudomonas aeruginosa. Catalytic and regulatory properties. European journal of biochemistry 52, Pubmed: 240684
  • Hu L, Mulfinger LM, Phillips AT (1987)Purification and properties of formylglutamate amidohydrolase from Pseudomonas putida. Journal of bacteriology 169, Pubmed: 3308850
  • Miyake M, Innami T, Kakimoto Y (1983)A beta-citryl-L-glutamate-hydrolysing enzyme in rat testes. Biochimica et biophysica acta 760, Pubmed: 6414521
Synthesis Reference: Borek, Blanche Ann; Waelsch, Heinrich. The enzymic degradation of histidine. Journal of Biological Chemistry (1953), 205 459-74.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB03470
PUBCHEM5459967
CHEMSPIDER19975498
CHEBI17684
LIGAND-CPDC01045