ChemFOnt: Showing chemical card for gamma-Glutamylphenylalanine (CFc000000462)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:51 UTC

Chemfont ID

CFc000000462

Molecule Identification

Common Name

gamma-Glutamylphenylalanine

Definition

1611

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid	ChEBI
L-gamma-Glu-L-phe	ChEBI
L-gamma-Glutamyl-L-phenylalanine	ChEBI
N-(gamma-L-Glutamyl)phenylalanine	ChEBI
N-L-gamma-Glutamyl-3-phenyl-L-alanine	ChEBI
N-L-gamma-Glutamyl-L-phenylalanine	ChEBI
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate	Generator
L-g-Glu-L-phe	Generator
L-Γ-glu-L-phe	Generator
L-g-Glutamyl-L-phenylalanine	Generator
L-Γ-glutamyl-L-phenylalanine	Generator
N-(g-L-Glutamyl)phenylalanine	Generator
N-(Γ-L-glutamyl)phenylalanine	Generator
N-L-g-Glutamyl-3-phenyl-L-alanine	Generator
N-L-Γ-glutamyl-3-phenyl-L-alanine	Generator
N-L-g-Glutamyl-L-phenylalanine	Generator
N-L-Γ-glutamyl-L-phenylalanine	Generator
g-Glutamylphenylalanine	Generator
Γ-glutamylphenylalanine	Generator
gamma-Glu-phe	MeSH
γ-Glu-Phe	HMDB, Generator
γ-L-Glu-L-Phe	HMDB
γ-L-Glutamyl-L-phenylalanine	HMDB
N-γ-Glutamylphenylalanine	HMDB
N-L-γ-Glutamylphenylalanine	HMDB
gamma-L-Glu-L-Phe	HMDB
gamma-L-Glutamyl-L-phenylalanine	HMDB
N-gamma-Glutamylphenylalanine	HMDB
N-L-gamma-Glutamylphenylalanine	HMDB
H-γ-Glu-Phe-OH	HMDB
H-gamma-Glu-Phe-OH	HMDB
gamma-Glutamylphenylalanine	HMDB, ChEBI
N-gamma-L-Glutamyl-L-phenylalanine	HMDB
N-γ-L-Glutamyl-L-phenylalanine	HMDB
g-Glu-Phe	Generator, HMDB

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.3031

Monoisotopic Molecular Weight

294.121571696

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid

Traditional Name

gamma-glutamylphenylalanine

CAS Registry Number

7432-24-8

SMILES

N[C@@H](CCC(=O)N[C@@H](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)/t10-,11-/m0/s1

InChI Key

XHHOHZPNYFQJKL-QWRGUYRKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Kidney (HMDB: HMDB0000594)
Placenta (HMDB: HMDB0000594)

Excreta

Biofluid or Excreta

Urine (PMID: 466810)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0000594)

Source

Endogenous

Endogenous (HMDB: HMDB0000594)

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	0.61 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.82	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	8	ChemAxon
Refractivity	73.2 m³·mol⁻¹	ChemAxon
Polarizability	29.7 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

HMDB0029562

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112161

KNApSAcK ID

Not Available

Chemspider ID

99868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

111299

PDB ID

Not Available

ChEBI ID

89582

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Bodnaryk, Robert P. Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine. Insect Biochemistry (1972), 2(1), 49-52.

Showing chemical card for gamma-Glutamylphenylalanine (CFc000000462)

MOL for CFc000000462 (gamma-Glutamylphenylalanine)

3D MOL for CFc000000462 (gamma-Glutamylphenylalanine)

3D SDF for CFc000000462 (gamma-Glutamylphenylalanine)

3D-SDF for CFc000000462 (gamma-Glutamylphenylalanine)

PDB for CFc000000462 (gamma-Glutamylphenylalanine)

3D PDB for CFc000000462 (gamma-Glutamylphenylalanine)

SMILES for CFc000000462 (gamma-Glutamylphenylalanine)

INCHI for CFc000000462 (gamma-Glutamylphenylalanine)

Structure for CFc000000462 (gamma-Glutamylphenylalanine)

3D Structure for CFc000000462 (gamma-Glutamylphenylalanine)