Record Information
Version2.0
Creation Date2012-05-31 14:21:08 -0600
Update Date2015-06-03 17:19:03 -0600
Secondary Accession Numbers
  • ECMDB12230
Identification
Name:gamma-Glutamyl-L-putrescine
DescriptionGamma-glutamyl-L-putrescine is involved in the putrescine degradation pathway.
Structure
Thumb
Synonyms:
  • γ-Glu-Put
  • γ-glutamylputrescine
  • g-Glu-put
  • g-Glutamyl-L-putrescine
  • g-Glutamyl-putrescine
  • g-Glutamylputrescine
  • g-L Glutamylputrescine
  • g-L-Glutamylputrescine
  • Gamma-Glu-put
  • Gamma-Glutamyl-putrescine
  • Gamma-Glutamylputrescine
  • Gamma-L Glutamylputrescine
  • Gamma-L-Glutamylputrescine
  • N-(4-Aminobutyl)-L-glutamine
  • γ-Glu-put
  • γ-Glutamyl-L-putrescine
  • γ-Glutamyl-putrescine
  • γ-Glutamylputrescine
  • γ-L Glutamylputrescine
  • γ-L-Glutamylputrescine
Chemical Formula:C9H19N3O3
Weight:Average: 217.2655
Monoisotopic: 217.142641489
InChI Key:WKGTVHGVLRCTCF-ZETCQYMHSA-N
InChI:InChI=1S/C9H19N3O3/c10-5-1-2-6-12-8(13)4-3-7(11)9(14)15/h7H,1-6,10-11H2,(H,12,13)(H,14,15)/t7-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-[(4-aminobutyl)carbamoyl]butanoic acid
Traditional IUPAC Name:gamma-L-glutamylputrescine
SMILES:NCCCCNC(=O)CC[C@H](N)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
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • 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 Solubility17.7 g/LALOGPS
logP-3.4ALOGPS
logP-4.3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity55.47 m³·mol⁻¹ChemAxon
Polarizability23.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Putrescine Degradation IIPW002054 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:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9220000000-3692792059eddd8d9f96View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-aab563ac8a20e723243fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g4r-5960000000-6180b7658814525b0797View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9600000000-f8149e3203a0b1d7acedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-e06ccbcc40dccfcaffc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1690000000-e23420d285d0b5032a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kk-6920000000-aab09866c47cb1656ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9200000000-14640b35aad6a5f4e420View 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 ID48005
HMDB IDHMDB12230
Pubchem Compound ID20841830
Kegg IDC15699
ChemSpider ID20148392
Wikipedia IDNot Available
BioCyc IDGAMMA-GLUTAMYL-PUTRESCINE
EcoCyc IDGAMMA-GLUTAMYL-PUTRESCINE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Involved in the breakdown of putrescine via the oxidation of L-glutamylputrescine
Gene Name:
puuB
Uniprot ID:
P37906
Molecular weight:
47169
Reactions
Gamma-glutamylputrescine + H(2)O + O(2) = Gamma-glutamyl-gamma-aminobutyraldehyde + NH(3) + H(2)O(2).
General function:
Involved in glutamate-ammonia ligase activity
Specific function:
Involved in the breakdown of putrescine via the biosynthesis of gamma-L-glutamylputrescine
Gene Name:
puuA
Uniprot ID:
P78061
Molecular weight:
53177
Reactions
ATP + L-glutamate + putrescine = ADP + phosphate + gamma-L-glutamylputrescine.