4-(γ-Glutamylamino)butanoic acid

4-(γ-Glutamylamino)butanoic acid

Names
Preferred IUPAC name 2-Amino-5-[(4-hydroxy-4-oxobutyl)amino]-5-oxopentanoic acid
Systematic IUPAC name 4-Amino-5-((3-carboxypropyl)amino)-5-oxopentanoic acid
Other names 2-Amino-5-(3-carboxypropylamino)-5-oxopentanoic acid[1] 4-(Glutam-5-ylamino)butanoic acid γ-Glutamyl-γ-aminobutyric acid
Identifiers
CAS Number	5105-96-4 S
3D model (Jmol)	Interactive image Interactive image
Abbreviations	Glutamyl-GABA Glu-GABA γ-Glutamyl-GABA γ-Glu-γ-Abu
Beilstein Reference	2418119
ChEBI	CHEBI:49260
ChEMBL	ChEMBL269574
ChemSpider	315618
KEGG	C15767
PubChem	355553 23724570 S
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) Key: MKYPKZSGLSOGLL-UHFFFAOYSA-N
SMILES NC(CCc(:[o]):[nH]CCCc(:[o]):[oH])c(:[o]):[oH] NC(CCC(=O)NCCCC(O)=O)C(O)=O
Properties
Chemical formula	C9H16N2O5
Molar mass	232.24 g·mol^−1
log P	−1.434
Acidity (pKa)	2.223
Basicity (pKb)	11.777
Related compounds
Related alkanoic acids	Hopantenic acid Hypusine Saccharopine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-(γ-Glutamylamino)butanoic acid is molecule that consists of L-glutamate conjugated to γ-aminobutyric acid (GABA). It is the substrate of the enzyme γ-glutamyl-γ-aminobutyrate hydrolase, which is involved in the biosynthesis of polyamines.^[2]

References

1. "NSC609423 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 July 2012.
2. Kurihara S, Oda S, Kato K, Kim HG, Koyanagi T, Kumagai H, Suzuki H (2005). "A novel putrescine utilization pathway involves gamma-glutamylated intermediates of Escherichia coli K-12". J. Biol. Chem. 280: 4602–8. doi:10.1074/jbc.M411114200. PMID 15590624.