ChemFOnt: Showing chemical card for Glutamylalanine (CFc000001962)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:43 UTC

Chemfont ID

CFc000001962

Molecule Identification

Common Name

Glutamylalanine

Definition

Glutamylalanine is a naturally occurring dipeptide, composed of glutamate and alanine. Glutamylalanine is essential in the supply of glutamate to human erythrocytes. Human erythrocytes are essentially impermeable to glutamate and yet there is a continual requirement for the amino acid for glutathione synthesis. In addition, the intracellular glutamate concentration is approximately five times that of plasma. Glutamylalanine enters the human erythrocyte through saturable membrane-transport systems describable by Michaelis-Menten kinetics. The cytosolic red cell peptidases have a vast capacity to hydrolyse the dipeptide in a process also describable by simple Michaelis-Menten kinetics. The transport process is the rate-determining step in the pathway leading to the production of intracellular glutamate from extracellular glutamylalanine. Glutamylalanine is transported by the human oligopeptide transporter, hPepT1, situated in the small intestine, which is involved in the absorption of nutrient oligopeptides and transports numerous di- and tripeptides. This active transport is being tested for use as a strategy to increase the permeability across the intestine for larger biologically active molecules with low intestinal permeability, in a therapeutic attempt to transport dipeptide-coupled active drug substances via hPepT1 (PMID: 2860897 , 11557350 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glu-ala	MeSH
a-Glutamylalanine	HMDB
a-L-Glutamyl-L-alanine	HMDB
alpha-Glutamylalanine	HMDB
alpha-L-Glutamyl-L-alanine	HMDB
L-alpha-Glutamyl-L-amino acid	HMDB
L-Glutamyl-L-alanine	HMDB
N-L-alpha-Glutamyl-L-alanine	HMDB

Chemical Formula

C₈H₁₄N₂O₅

Average Molecular Weight

218.2072

Monoisotopic Molecular Weight

218.090271568

IUPAC Name

4-amino-4-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

glu-ala

CAS Registry Number

21064-18-6

SMILES

CC(N=C(O)C(N)CCC(O)=O)C(O)=O

InChI Identifier

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

InChI Key

JZDHUJAFXGNDSB-UHFFFAOYSA-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
Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Amino fatty 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
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Amine
Primary amine
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0003764)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.28 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	49.11 m³·mol⁻¹	ChemAxon
Polarizability	20.97 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023223

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Sachs, Howard; Brand, Erwin. Optical rotation of peptides. VIII. Glutamic acid tripeptides. Journal of the American Chemical Society (1954), 76 1811-14.

Showing chemical card for Glutamylalanine (CFc000001962)

MOL for CFc000001962 (Glutamylalanine)

3D MOL for CFc000001962 (Glutamylalanine)

3D SDF for CFc000001962 (Glutamylalanine)

3D-SDF for CFc000001962 (Glutamylalanine)

PDB for CFc000001962 (Glutamylalanine)

3D PDB for CFc000001962 (Glutamylalanine)

SMILES for CFc000001962 (Glutamylalanine)

INCHI for CFc000001962 (Glutamylalanine)

Structure for CFc000001962 (Glutamylalanine)

3D Structure for CFc000001962 (Glutamylalanine)