ChemFOnt: Showing chemical card for gamma-L-Glutamyl-L-phenylalanine (CFc000333213)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:05 UTC

Chemfont ID

CFc000333213

Molecule Identification

Common Name

gamma-L-Glutamyl-L-phenylalanine

Definition

Glutamylphenylalanine is a gamma-glutamyl derivative. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID 237763 ). It can be detected in urine of patients with phenylketonuria, which is a is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine . gamma-L-Glutamyl-L-phenylalanine is found in soft-necked garlic.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
gamma-Glu-phe	ChEBI
g-Glu-phe	Generator
Γ-glu-phe	Generator
N-g-L-Glutamyl-L-phenylalanine	Generator
N-Γ-L-glutamyl-L-phenylalanine	Generator
gamma-Glutamylphenylalanine	MeSH
gamma-Glutamylphenylalanine, (D-phe-D-glu)-isomer	MeSH
gamma-Glutamylphenylalanine, (L-phe-D-glu)-isomer	MeSH

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.3031

Monoisotopic Molecular Weight

294.121571696

IUPAC Name

2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid

CAS Registry Number

7432-24-8

SMILES

NC(CCC(O)=NC(CC1=CC=CC=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)

InChI Key

XHHOHZPNYFQJKL-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
Gamma-glutamyl alpha-amino acid
Phenylalanine or derivatives
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:82966 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB00594)

Food

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.54	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	8	ChemAxon
Refractivity	73.73 m³·mol⁻¹	ChemAxon
Polarizability	29.25 Å³	ChemAxon
Number of Rings	1	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

FDB000716

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

558649

PDB ID

Not Available

ChEBI ID

82966

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for gamma-L-Glutamyl-L-phenylalanine (CFc000333213)

MOL for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

3D MOL for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

3D SDF for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

3D-SDF for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

PDB for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

3D PDB for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

SMILES for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

INCHI for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

Structure for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)

3D Structure for CFc000333213 (gamma-L-Glutamyl-L-phenylalanine)