ChemFOnt: Showing chemical card for (5-L-Glutamyl)-L-amino acid (CFc000041785)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:43:58 UTC

Chemfont ID

CFc000041785

Molecule Identification

Common Name

(5-L-Glutamyl)-L-amino acid

Definition

gamma-Glutamylalanine, also known as 5-L-glutamyl-L-alanine or L-gamma-glu-L-ala, 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. gamma-Glutamylalanine exists in all eukaryotes, ranging from yeast to plants to humans. gamma-Glutamylalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make gamma-glutamylalanine a potential biomarker for the consumption of these foods. gamma-Glutamylalanine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on gamma-Glutamylalanine.

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

Exogenous (HMDB: HMDB0061369)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

5-Oxoprolinuria (PathBank: SMP0120446)
Gamma-Glutamyltranspeptidase Deficiency (PathBank: SMP0120566)
Gamma-Glutamyltransferase Deficiency (PathBank: SMP0120480)
Glutathione Synthetase Deficiency (PathBank: SMP0120485)
5-Oxoprolinase Deficiency (PathBank: SMP0120565)

Metabolic pathway

Glutathione Metabolism (PathBank: SMP0063622)

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