ChemFOnt: Showing chemical card for gamma-Glutamylalanine (CFc000002686)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:37 UTC

Chemfont ID

CFc000002686

Molecule Identification

Common Name

gamma-Glutamylalanine

Definition

gamma-Glutamylalanine is a dipeptide composed of gamma-glutamate and alanine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylalanine is a natural substrate of the enzyme (5-L-glutamyl)-L-amino acid 5-glutamyltransferase (cyclizing) (g-glutamylcyclotransferase, EC 2.3.2.2) in the glutathione metabolism pathway, which cleaves gamma-glutamylalanine to produce L-5-oxoproline. gamma-Glutamylcyclotransferase is widely distributed in both human and animal tissues where it catalyzes the scission of the y-peptide bonds of many different gamma-glutamyl-amino acids and gamma-glutamyl-gamma-glutamyl-amino acids. The latter are 'better' substrates of the enzyme than the corresponding gamma-glutamyl-amino acids (PMID: 2570694 , 2893631 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-L-Glutamyl-L-alanine	ChEBI
gamma-L-Glutamyl-L-alanine	ChEBI
L-gamma-Glu-L-ala	ChEBI
N-L-gamma-Glutamyl-L-alanine	ChEBI
g-L-Glutamyl-L-alanine	Generator
Γ-L-glutamyl-L-alanine	Generator
L-g-Glu-L-ala	Generator
L-Γ-glu-L-ala	Generator
N-L-g-Glutamyl-L-alanine	Generator
N-L-Γ-glutamyl-L-alanine	Generator
g-Glutamylalanine	Generator
Γ-glutamylalanine	Generator
γ-Glu-Ala	HMDB
γ-L-Glu-L-Ala	HMDB
L-γ-Glutamyl-L-alanine	HMDB
N-γ-Glutamylalanine	HMDB
N-L-γ-Glutamylalanine	HMDB
gamma-Glu-Ala	HMDB
gamma-L-Glu-L-Ala	HMDB
L-gamma-Glutamyl-L-alanine	HMDB
N-gamma-Glutamylalanine	HMDB
N-L-gamma-Glutamylalanine	HMDB
gamma-Glutamylalanine	HMDB, ChEBI
5-L-Glutamylalanine	HMDB
g-Glu-Ala	HMDB
N-γ-L-Glutamyl-L-alanine	HMDB
N-gamma-L-Glutamyl-L-alanine	HMDB

Chemical Formula

C₈H₁₄N₂O₅

Average Molecular Weight

218.2072

Monoisotopic Molecular Weight

218.090271568

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid

Traditional Name

g-glu-ala

CAS Registry Number

5875-41-2

SMILES

C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

WQXXXVRAFAKQJM-WHFBIAKZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alanine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Amine
Primary amine
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylalanine (CHEBI:50619 )

Functional Ontology

Not Available

Placenta (HMDB: HMDB0006248)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0006248)

Source

Endogenous

Endogenous (HMDB: HMDB0006248)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glutathione Metabolism (HMDB: HMDB0006248)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-3.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.93	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	6	ChemAxon
Refractivity	48.59 m³·mol⁻¹	ChemAxon
Polarizability	20.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon