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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:08 -0600
Update Date	2015-06-03 17:19:03 -0600
Secondary Accession Numbers	ECMDB12230
Identification
Name:	gamma-Glutamyl-L-putrescine
Description	Gamma-glutamyl-L-putrescine is involved in the putrescine degradation pathway.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae81e7d8> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Glutamine and derivatives
Alternative Parents	L-alpha-amino acids N-acyl amines Fatty acids and conjugates Secondary carboxylic acid amides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	non-proteinogenic L-alpha-amino acid (CHEBI:48005 ) L-glutamine derivative (CHEBI:48005 ) gamma-glutamylputrescine (CHEBI:48005 )
Physical Properties
State:	Solid
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 17.7 g/L ALOGPS logP -3.4 ALOGPS logP -4.3 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 2.24 ChemAxon pKa (Strongest Basic) 10 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 118.44 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 55.47 m³·mol⁻¹ ChemAxon Polarizability 23.61 ų ChemAxon Number of Rings 0 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:	Adenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + Phosphate gamma-Glutamyl-L-putrescine + Water + Oxygen > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium Adenosine triphosphate + L-Glutamate + Putrescine <> ADP + Phosphate + gamma-Glutamyl-L-putrescine gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide Putrescine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP + Phosphate Adenosine triphosphate + L-Glutamate + Putrescine > ADP + Inorganic phosphate + gamma-Glutamyl-L-putrescine gamma-Glutamyl-L-putrescine + Water + Oxygen > Gamma-glutamyl-gamma-aminobutyraldehyde + Ammonia + Hydrogen peroxide Putrescine + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Phosphate + Adenosine diphosphate + Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP gamma-Glutamyl-L-putrescine + Oxygen + Water > 4-(γ-glutamylamino)butanal + Ammonium + Hydrogen peroxide gamma-Glutamyl-L-putrescine + Oxygen + Hydrogen ion > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide
SMPDB Pathways:	Putrescine Degradation II PW002054 arginine metabolism PW000790 ornithine metabolism PW000791
KEGG Pathways:	Arginine and proline metabolism ec00330 Metabolic pathways eco01100
EcoCyc Pathways:	putrescine degradation II PWY0-1221
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00e9-9220000000-3692792059eddd8d9f96 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-8900000000-aab563ac8a20e723243f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0g4r-5960000000-6180b7658814525b0797 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05g0-9600000000-f8149e3203a0b1d7aced View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0ab9-9000000000-e06ccbcc40dccfcaffc0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-1690000000-e23420d285d0b5032a09 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00kk-6920000000-aab09866c47cb1656ce2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0076-9200000000-14640b35aad6a5f4e420 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014j-0490000000-6bc9f244b715f8e50983 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-4970000000-8697edbdcab7a385d0d5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9300000000-237772c5fd2e73d9777b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-2090000000-cfa5ea65ae63fcdc766b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-008i-8920000000-15903d56fd570da0c9a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-9000000000-3a89ef16c334673591db View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 48005 HMDB ID HMDB12230 Pubchem Compound ID 20841830 Kegg ID C15699 ChemSpider ID 20148392 Wikipedia ID Not Available BioCyc ID GAMMA-GLUTAMYL-PUTRESCINE EcoCyc ID GAMMA-GLUTAMYL-PUTRESCINE

Enzymes