ECMDB: 4-(Glutamylamino) butanoate (ECMDB12161) (M2MDB000824)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (69)

Record Information

Version

2.0

Creation Date

2012-05-31 14:20:49 -0600

Update Date

2015-06-03 17:19:02 -0600

Secondary Accession Numbers

ECMDB12161

Identification

Name:

4-(Glutamylamino) butanoate

Description

4-(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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:49260 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	12.1 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-3.9	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.3	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	53.55 m³·mol⁻¹	ChemAxon
Polarizability	23.13 Å³	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:

SMPDB Pathways:

L-glutamate metabolism	PW000789
arginine metabolism	PW000790
ornithine metabolism	PW000791

KEGG Pathways:

Arginine and proline metabolism ec00330

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 (Non-derivatized) - 70eV, Positive	splash10-0ulc-7910000000-b180673c226650030a25	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g3-9623000000-8aa3ee981fb5e1add764	View in MoNA
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	splash10-014r-3950000000-9d8d39dc6519b3171e0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6900000000-385a19df9909a7ad7991	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-9100000000-c0d18862069fd0662ee5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0490000000-8d29317946344396fe2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0il0-3940000000-a57dd6eea481f1b93528	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0537-9300000000-989347942071d912cb78	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsr-3590000000-7bb6b7ddd62b988a0e03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-9400000000-1884f3bf1a0839dd5d37	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053i-9100000000-214041043edf236444ef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2790000000-b44ba12e152e525d33bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0il1-2930000000-5d3c67d257132eddef13	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f8c-9400000000-40c737608034c80a7087	View in MoNA
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
1D NMR	1H 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	49260
HMDB ID	HMDB12161
Pubchem Compound ID	23724570
Kegg ID	C15767
ChemSpider ID	21865667
Wikipedia ID	Not Available
BioCyc ID	CPD-9000
EcoCyc ID	CPD-9000

Enzymes

Protein Details

1. Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenase

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.

Protein Details

2. Glutamate decarboxylase alpha

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).

Protein Details

3. Glutamate decarboxylase beta

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).

Protein Details

4. Gamma-glutamyl-gamma-aminobutyrate hydrolase

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.

4-(Glutamylamino) butanoate (ECMDB12161) (M2MDB000824)

Structure for #<Compound:0xad5d06f8>

Enzymes

Reactions

Reactions

Reactions

Reactions