ChemFOnt: Showing chemical card for gamma-Glutamylglycine (CFc000007245)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:28 UTC

Chemfont ID

CFc000007245

Molecule Identification

Common Name

gamma-Glutamylglycine

Definition

gamma-Glutamylglycine is one of the dipeptides that is commonly produced from polypeptides by the action of the enzyme dipeptidyl peptidase. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin. gamma-Glutamylglycine is an excitatory amino acid receptor antagonist with a structure similar to gamma-aminobutyric acid (GABA) (PMID: 6146532 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-L-Glutamylglycine	ChEBI
gamma-L-Glu-gly	ChEBI
L-gamma-Glu-gly	ChEBI
N-L-gamma-Glutamylglycine	ChEBI
g-L-Glu-gly	Generator
Γ-L-glu-gly	Generator
L-g-Glu-gly	Generator
L-Γ-glu-gly	Generator
N-L-g-Glutamylglycine	Generator
N-L-Γ-glutamylglycine	Generator
g-Glutamylglycine	Generator
Γ-glutamylglycine	Generator
γ-Glu-Gly	HMDB, Generator
γ-L-Glutamylglycine	HMDB
L-γ-Glutamylglycine	HMDB
N-γ-Glutamylglycine	HMDB
N-γ-L-Glutamylglycine	HMDB
gamma-Glu-Gly	HMDB
gamma-L-Glutamylglycine	HMDB
L-gamma-Glutamylglycine	HMDB
N-gamma-Glutamylglycine	HMDB
N-gamma-L-Glutamylglycine	HMDB
N-(Carboxymethyl)-glutamine	HMDB
L-N-(Carboxymethyl)-glutamine	HMDB
gamma-Glutamylglycine	HMDB, MeSH
5-L-Glutamyl-glycine	HMDB
gamma-Glutamyl glycine	HMDB
gamma-L-Glutamyl-glycine	HMDB
N-L-gamma-Glutamyl-glycine	HMDB
g-Glu-Gly	Generator, HMDB

Chemical Formula

C₇H₁₂N₂O₅

Average Molecular Weight

204.1806

Monoisotopic Molecular Weight

204.074621504

IUPAC Name

(2S)-2-amino-4-[(carboxymethyl)carbamoyl]butanoic acid

Traditional Name

(2S)-2-amino-4-(carboxymethylcarbamoyl)butanoic acid

CAS Registry Number

1948-29-4

SMILES

N[C@@H](CCC(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73845 )

Functional Ontology

Not Available

Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0011667)

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	21.2 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-4.4	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	1.83	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	44.09 m³·mol⁻¹	ChemAxon
Polarizability	18.82 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

HMDB0011667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028356

KNApSAcK ID

Not Available

Chemspider ID

145071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165527

PDB ID

Not Available

ChEBI ID

73845

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for gamma-Glutamylglycine (CFc000007245)

MOL for CFc000007245 (gamma-Glutamylglycine)

3D MOL for CFc000007245 (gamma-Glutamylglycine)

3D SDF for CFc000007245 (gamma-Glutamylglycine)

3D-SDF for CFc000007245 (gamma-Glutamylglycine)

PDB for CFc000007245 (gamma-Glutamylglycine)

3D PDB for CFc000007245 (gamma-Glutamylglycine)

SMILES for CFc000007245 (gamma-Glutamylglycine)

INCHI for CFc000007245 (gamma-Glutamylglycine)

Structure for CFc000007245 (gamma-Glutamylglycine)

3D Structure for CFc000007245 (gamma-Glutamylglycine)