ChemFOnt: Showing chemical card for D-Glutamine (CFc000001882)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:37 UTC

Chemfont ID

CFc000001882

Molecule Identification

Common Name

D-Glutamine

Definition

D-Glutamine, also known as DGN or D glutamine, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. Supplementation does not appear to be useful in adults or children with Crohn's disease or inflammatory bowel disease, but clinical studies as of 2016 were underpowered. D-Glutamine is a drug. D-Glutamine exists in all living species, ranging from bacteria to humans. D-Glutamine is a potentially toxic compound. Adverse effects of glutamine have been described for people receiving home parenteral nutrition and those with liver-function abnormalities. Glutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood-brain barrier. Glutamine can exist in either of two enantiomeric forms, L-glutamine and D-glutamine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,5-Diamino-5-oxopentanoic acid	ChEBI
(2R)-2-Amino-4-carbamoylbutanoic acid	ChEBI
(R)-2,5-Diamino-5-oxopentanoic acid	ChEBI
D-2-Aminoglutaramic acid	ChEBI
D-Glutamin	ChEBI
D-Glutaminsaeure-5-amid	ChEBI
DGN	ChEBI
(2R)-2,5-Diamino-5-oxopentanoate	Generator
(2R)-2-Amino-4-carbamoylbutanoate	Generator
(R)-2,5-Diamino-5-oxopentanoate	Generator
D-2-Aminoglutaramate	Generator
Nutrestore	HMDB
L-Glutamine	HMDB
D Glutamine	HMDB
L Glutamine	HMDB
Glutamine	HMDB

Chemical Formula

C₅H₁₀N₂O₃

Average Molecular Weight

146.1445

Monoisotopic Molecular Weight

146.069142196

IUPAC Name

(2R)-2-amino-4-carbamoylbutanoic acid

Traditional Name

D-glutamine

CAS Registry Number

5959-95-5

SMILES

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

InChI Identifier

InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1

InChI Key

ZDXPYRJPNDTMRX-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:17061 )
glutamine (CHEBI:17061 )
Other amino acids (C00819 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0003423)
Blood (HMDB: HMDB0003423)

Cellular substructure

Cytoplasm (HMDB: HMDB0003423)
Membrane (HMDB: HMDB0003423)

Source

Exogenous

Exogenous (HMDB: HMDB0003423)

Food

Animal origin

Poultry

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)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Endogenous

Endogenous (HMDB: HMDB0003423)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Lysinuric Protein Intolerance (HMDB: HMDB0003423)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003423)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	97.8 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-4	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.11 m³·mol⁻¹	ChemAxon
Polarizability	13.59 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

HMDB0003423

DrugBank ID

DB02174

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023171

KNApSAcK ID

Not Available

Chemspider ID

128633

KEGG Compound ID

C00819

BioCyc ID

GLUTAMIDE

BiGG ID

Not Available

Wikipedia Link

Glutamine

METLIN ID

6926

PubChem Compound

145815

PDB ID

Not Available

ChEBI ID

17061

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Qian, Shao-Song; Wu, Xiao-Yan; Li, Jia-You; Liu, Yi; Chen, Ran; Jiao, Qing-Cai. Preparation of D-glutamine from glutamic acid. Youji Huaxue (2006), 26(4), 514-517.

Showing chemical card for D-Glutamine (CFc000001882)

MOL for CFc000001882 (D-Glutamine)

3D MOL for CFc000001882 (D-Glutamine)

3D SDF for CFc000001882 (D-Glutamine)

3D-SDF for CFc000001882 (D-Glutamine)

PDB for CFc000001882 (D-Glutamine)

3D PDB for CFc000001882 (D-Glutamine)

SMILES for CFc000001882 (D-Glutamine)

INCHI for CFc000001882 (D-Glutamine)

Structure for CFc000001882 (D-Glutamine)

3D Structure for CFc000001882 (D-Glutamine)