Record Information
Version2.0
Creation Date2012-05-31 14:20:49 -0600
Update Date2015-06-03 17:19:02 -0600
Secondary Accession Numbers
  • ECMDB12161
Identification
Name:4-(Glutamylamino) butanoate
Description4-(Glutamylamino) butanoate is a polyamine that is an intermediate in putrescine degradation . Polyamines (the most common of which are putrescine , spermidine , and spermine ), a group of positively charged small molecules present in virtually all living organisms, have been implicated in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. Although polyamines are clearly necessary for optimal cell growth, a surplus of polyamines can cause inhibition of growth and protein synthesis, and thus a balance is desired between the production and breakdown of polyamines. In putrescine degradation , 4-(Glutamylamino) butanoate is a substrate for gamma-glutamyl-gamma-aminobutyrate hydrolase (puuD) and can be generated from the hydrolysis of gamma-glutamyl-gamma-aminobutyraldehyde.
Structure
Thumb
Synonyms:
  • γ-glu-GABA
  • γ-glutamyl-γ-aminobutanoate
  • γ-glutamyl-γ-aminobutanoic acid
  • γ-glutamyl-γ-aminobutyrate
  • γ-glutamyl-γ-aminobutyric acid
  • 4-(Glutamylamino) butanoic acid
  • 4-(Glutamylamino)butanoate
  • 4-(Glutamylamino)butanoic acid
  • 4-(L-g-glutamylamino)Butanoate
  • 4-(L-g-glutamylamino)Butanoic acid
  • 4-(L-gamma-Glutamylamino)butanoate
  • 4-(L-gamma-Glutamylamino)butanoic acid
  • 4-(L-Glutam-5-ylamino)butanoate
  • 4-(L-Glutam-5-ylamino)butanoic acid
  • 4-(L-γ-glutamylamino)Butanoate
  • 4-(L-γ-glutamylamino)Butanoic acid
  • g Glutamyl gaba
  • g-Glu-gaba
  • g-Glutamyl-g aminobutyrate
  • g-Glutamyl-g aminobutyric acid
  • g-Glutamyl-g-aminobutanoate
  • g-Glutamyl-g-aminobutanoic acid
  • g-Glutamyl-g-aminobutyrate
  • g-Glutamyl-g-aminobutyric acid
  • g-Glutamyl-gaba
  • g-L-Glu-g-abu
  • g-L-Glutamyl-g-aminobutyrate
  • g-L-Glutamyl-g-aminobutyric acid
  • Gamma Glutamyl gaba
  • Gamma-Glu-gaba
  • Gamma-Glutamyl-gaba
  • Gamma-Glutamyl-gamma aminobutyrate
  • Gamma-Glutamyl-gamma aminobutyric acid
  • Gamma-Glutamyl-gamma-aminobutanoate
  • Gamma-Glutamyl-gamma-aminobutanoic acid
  • Gamma-Glutamyl-gamma-aminobutyrate
  • Gamma-Glutamyl-gamma-aminobutyric acid
  • Gamma-L-Glu-gamma-abu
  • Gamma-L-Glutamyl-gamma-aminobutyrate
  • Gamma-L-Glutamyl-gamma-aminobutyric acid
  • Glugaba
  • Glutamylgaba
  • N(5)-(3-Carboxypropyl)-L-glutamine
  • γ Glutamyl gaba
  • γ-Glu-gaba
  • γ-Glutamyl-gaba
  • γ-Glutamyl-γ aminobutyrate
  • γ-Glutamyl-γ aminobutyric acid
  • γ-Glutamyl-γ-aminobutanoate
  • γ-Glutamyl-γ-aminobutanoic acid
  • γ-Glutamyl-γ-aminobutyrate
  • γ-Glutamyl-γ-aminobutyric acid
  • γ-L-Glu-γ-abu
  • γ-L-Glutamyl-γ-aminobutyrate
  • γ-L-Glutamyl-γ-aminobutyric acid
Chemical Formula:C9H16N2O5
Weight:Average: 232.2337
Monoisotopic: 232.105921632
InChI Key:MKYPKZSGLSOGLL-LURJTMIESA-N
InChI:InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1
CAS number:5105-96-4
IUPAC Name:(2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid
Traditional IUPAC Name:glugaba
SMILES:N[C@@H](CCC(=O)NCCCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Gamma amino acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP-3.4ALOGPS
logP-3.9ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.3ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.55 m³·mol⁻¹ChemAxon
Polarizability23.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
L-glutamate metabolismPW000789 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
ornithine metabolismPW000791 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ulc-7910000000-b180673c226650030a25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9623000000-8aa3ee981fb5e1add764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-3950000000-9d8d39dc6519b3171e0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6900000000-385a19df9909a7ad7991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9100000000-c0d18862069fd0662ee5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0490000000-8d29317946344396fe2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0il0-3940000000-a57dd6eea481f1b93528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0537-9300000000-989347942071d912cb78View in MoNA
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 ID49260
HMDB IDHMDB12161
Pubchem Compound ID23724570
Kegg IDC15767
ChemSpider ID21865667
Wikipedia IDNot Available
BioCyc IDCPD-9000
EcoCyc IDCPD-9000

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Involved in the breakdown of putrescine. Was previously shown to have a weak but measurable ALDH enzyme activity that prefers NADP over NAD as coenzyme
Gene Name:
puuC
Uniprot ID:
P23883
Molecular weight:
53418
Reactions
Gamma-glutamyl-gamma-aminobutyraldehyde + NAD(+) + H(2)O = gamma-glutamyl-gamma-aminobutyrate + NADH.
An aldehyde + NAD(P)(+) + H(2)O = a carboxylate + NAD(P)H.
General function:
Involved in glutamate decarboxylase activity
Specific function:
Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:
gadA
Uniprot ID:
P69908
Molecular weight:
52685
Reactions
L-glutamate = 4-aminobutanoate + CO(2).
General function:
Involved in glutamate decarboxylase activity
Specific function:
Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:
gadB
Uniprot ID:
P69910
Molecular weight:
52668
Reactions
L-glutamate = 4-aminobutanoate + CO(2).
General function:
Involved in hydrolase activity
Specific function:
Involved in the breakdown of putrescine via hydrolysis of the gamma-glutamyl linkage of gamma-glutamyl-gamma- aminobutyrate
Gene Name:
puuD
Uniprot ID:
P76038
Molecular weight:
28013
Reactions
4-(L-gamma-glutamylamino)butanoate + H(2)O = 4-aminobutanoate + L-glutamate.