ChemFOnt: Showing chemical card for gamma-Glutamyltryptophan (CFc000010413)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:50 UTC

Chemfont ID

CFc000010413

Molecule Identification

Common Name

gamma-Glutamyltryptophan

Definition

gamma-Glutamyltryptophan is a dipeptide composed of gamma-glutamate and tryptophan, 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-Glutamyltryptophan is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-gamma-Glu-L-TRP	ChEBI
L-g-Glu-L-TRP	Generator
L-Γ-glu-L-TRP	Generator
g-Glutamyltryptophan	Generator
Γ-glutamyltryptophan	Generator
gamma-Glutamate tryptophan dipeptide	HMDB
gamma-Glutamate-tryptophan dipeptide	HMDB
GE-W dipeptide	HMDB
GEW dipeptide	HMDB
GGlu-TRP	HMDB
L-gamma-Glutamyl-L-tryptophan	HMDB
gamma-L-Glutamyl-L-tryptophan	HMDB
gamma-Glutamyl-tryptophan	HMDB
gamma-Glu-TRP	HMDB
Bestim	HMDB
Γ-glu-TRP	HMDB
Γ-L-glu-L-TRP	HMDB
Γ-L-glutamyl-L-tryptophan	HMDB
L-Γ-glutamyl-L-tryptophan	HMDB
N-Γ-glutamyltryptophan	HMDB
N-L-Γ-glutamyltryptophan	HMDB
N-L-Γ-glutamyl-L-tryptophan	HMDB
gamma-L-Glu-L-TRP	HMDB
N-gamma-Glutamyltryptophan	HMDB
N-L-gamma-Glutamyltryptophan	HMDB
N-L-gamma-Glutamyl-L-tryptophan	HMDB
N-Γ-L-glutamyl-L-tryptophan	HMDB
N-gamma-L-Glutamyl-L-tryptophan	HMDB
g-Glu-TRP	HMDB
gamma-Glutamyltryptophan	HMDB, ChEBI

Chemical Formula

C₁₆H₁₉N₃O₅

Average Molecular Weight

333.344

Monoisotopic Molecular Weight

333.132470724

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

66471-20-3

SMILES

N[C@@H](CCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C16H19N3O5/c17-11(15(21)22)5-6-14(20)19-13(16(23)24)7-9-8-18-12-4-2-1-3-10(9)12/h1-4,8,11,13,18H,5-7,17H2,(H,19,20)(H,21,22)(H,23,24)/t11-,13-/m0/s1

InChI Key

CATMPQFFVNKDEY-AAEUAGOBSA-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 or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
L-alpha-amino acid
Indole or derivatives
Indole
Fatty acyl
N-acyl-amine
Benzenoid
Substituted pyrrole
Dicarboxylic acid or derivatives
Fatty amide
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Organoheterocyclic compound
Carboxylic acid
Azacycle
Primary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0029160)

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	0.35 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.98	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	84.29 m³·mol⁻¹	ChemAxon
Polarizability	33.64 Å³	ChemAxon
Number of Rings	2	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

HMDB0029160

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112152

KNApSAcK ID

Not Available

Chemspider ID

2302065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3038501

PDB ID

Not Available

ChEBI ID

133028

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for gamma-Glutamyltryptophan (CFc000010413)

MOL for CFc000010413 (gamma-Glutamyltryptophan)

3D MOL for CFc000010413 (gamma-Glutamyltryptophan)

3D SDF for CFc000010413 (gamma-Glutamyltryptophan)

3D-SDF for CFc000010413 (gamma-Glutamyltryptophan)

PDB for CFc000010413 (gamma-Glutamyltryptophan)

3D PDB for CFc000010413 (gamma-Glutamyltryptophan)

SMILES for CFc000010413 (gamma-Glutamyltryptophan)

INCHI for CFc000010413 (gamma-Glutamyltryptophan)

Structure for CFc000010413 (gamma-Glutamyltryptophan)

3D Structure for CFc000010413 (gamma-Glutamyltryptophan)