P. aeruginosa Metabolome Database: 4-(Glutamylamino) butanoate (PAMDB000824)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000824

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 PDB SMILES InChI View 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

Average Molecular Weight:

232.2337

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

################

Sub Class

################

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
D-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Amino fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
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 mg/mL	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:

4-(Glutamylamino) butanoate + Water <> gamma-Aminobutyric acid + L-Glutamate
gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <> 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH
gamma-Glutamyl-gamma-butyraldehyde + NAD + Water <> 4-(Glutamylamino) butanoate + NADH + Hydrogen ion
NAD(P)<sup>+</sup> + gamma-Glutamyl-gamma-butyraldehyde + Water > 4-(Glutamylamino) butanoate + NAD(P)H + Hydrogen ion
L-Glutamic acid + Hydrogen ion + L-Glutamate > Carbon dioxide + 4-(Glutamylamino) butanoate
4-(γ-glutamylamino)butanal + Water + NADP > 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH + NADPH
4-(Glutamylamino) butanoate + Water > L-Glutamic acid + gamma-Aminobutyric acid + L-Glutamate

Pathways:

Arginine and proline metabolism pae00330

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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

4-(Glutamylamino) butanoate (PAMDB000824)

Structure for 4-(Glutamylamino) butanoate (PAMDB000824)