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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 20:33:24 UTC

Update Date

2021-09-14 15:00:09 UTC

HMDB ID

HMDB0003423

Secondary Accession Numbers

HMDB03423

Metabolite Identification

Common Name

D-Glutamine

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

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

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.562	31661259
DarkChem	[M-H]-	125.365	31661259
DeepCCS	[M+H]+	128.008	30932474
DeepCCS	[M-H]-	124.179	30932474
DeepCCS	[M-2H]-	161.734	30932474
DeepCCS	[M+Na]+	137.147	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	126.3	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Glutamine	N[C@H](CCC(N)=O)C(O)=O	2078.4	Standard polar	33892256
D-Glutamine	N[C@H](CCC(N)=O)C(O)=O	1366.6	Standard non polar	33892256
D-Glutamine	N[C@H](CCC(N)=O)C(O)=O	1933.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Glutamine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](N)CCC(N)=O	1579.0	Semi standard non polar	33892256
D-Glutamine,1TMS,isomer #2	C[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O	1653.3	Semi standard non polar	33892256
D-Glutamine,1TMS,isomer #3	C[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O	1669.4	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C	1686.5	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C	1665.2	Standard non polar	33892256
D-Glutamine,2TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C	2602.5	Standard polar	33892256
D-Glutamine,2TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C	1666.2	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C	1748.1	Standard non polar	33892256
D-Glutamine,2TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C	2515.0	Standard polar	33892256
D-Glutamine,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O	1764.4	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O	1740.0	Standard non polar	33892256
D-Glutamine,2TMS,isomer #3	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O	2447.0	Standard polar	33892256
D-Glutamine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C	1843.8	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C	1718.8	Standard non polar	33892256
D-Glutamine,2TMS,isomer #4	C[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C	2792.5	Standard polar	33892256
D-Glutamine,2TMS,isomer #5	C[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C	1828.4	Semi standard non polar	33892256
D-Glutamine,2TMS,isomer #5	C[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C	1745.6	Standard non polar	33892256
D-Glutamine,2TMS,isomer #5	C[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C	2968.5	Standard polar	33892256
D-Glutamine,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1755.3	Semi standard non polar	33892256
D-Glutamine,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1800.8	Standard non polar	33892256
D-Glutamine,3TMS,isomer #1	C[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2040.1	Standard polar	33892256
D-Glutamine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	1850.3	Semi standard non polar	33892256
D-Glutamine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	1783.3	Standard non polar	33892256
D-Glutamine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	2470.5	Standard polar	33892256
D-Glutamine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1784.9	Semi standard non polar	33892256
D-Glutamine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1834.5	Standard non polar	33892256
D-Glutamine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2348.9	Standard polar	33892256
D-Glutamine,3TMS,isomer #4	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1893.9	Semi standard non polar	33892256
D-Glutamine,3TMS,isomer #4	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1815.5	Standard non polar	33892256
D-Glutamine,3TMS,isomer #4	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2221.7	Standard polar	33892256
D-Glutamine,3TMS,isomer #5	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1933.1	Semi standard non polar	33892256
D-Glutamine,3TMS,isomer #5	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1848.7	Standard non polar	33892256
D-Glutamine,3TMS,isomer #5	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2186.6	Standard polar	33892256
D-Glutamine,4TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1858.9	Semi standard non polar	33892256
D-Glutamine,4TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1890.5	Standard non polar	33892256
D-Glutamine,4TMS,isomer #1	C[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1931.7	Standard polar	33892256
D-Glutamine,4TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1915.5	Semi standard non polar	33892256
D-Glutamine,4TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1903.4	Standard non polar	33892256
D-Glutamine,4TMS,isomer #2	C[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1968.6	Standard polar	33892256
D-Glutamine,4TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2006.9	Semi standard non polar	33892256
D-Glutamine,4TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1947.5	Standard non polar	33892256
D-Glutamine,4TMS,isomer #3	C[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2068.1	Standard polar	33892256
D-Glutamine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2049.8	Semi standard non polar	33892256
D-Glutamine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2002.0	Standard non polar	33892256
D-Glutamine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1881.8	Standard polar	33892256
D-Glutamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(N)=O	1835.8	Semi standard non polar	33892256
D-Glutamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O	1912.9	Semi standard non polar	33892256
D-Glutamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O	1926.1	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	2151.7	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	2085.4	Standard non polar	33892256
D-Glutamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	2619.4	Standard polar	33892256
D-Glutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2130.4	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2135.4	Standard non polar	33892256
D-Glutamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2540.0	Standard polar	33892256
D-Glutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2259.2	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2117.9	Standard non polar	33892256
D-Glutamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2451.5	Standard polar	33892256
D-Glutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2290.7	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2139.0	Standard non polar	33892256
D-Glutamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](CCC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2699.8	Standard polar	33892256
D-Glutamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2252.5	Semi standard non polar	33892256
D-Glutamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2171.7	Standard non polar	33892256
D-Glutamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2775.6	Standard polar	33892256
D-Glutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2422.6	Semi standard non polar	33892256
D-Glutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2352.8	Standard non polar	33892256
D-Glutamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2348.0	Standard polar	33892256
D-Glutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2503.3	Semi standard non polar	33892256
D-Glutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2404.1	Standard non polar	33892256
D-Glutamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2582.3	Standard polar	33892256
D-Glutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2438.1	Semi standard non polar	33892256
D-Glutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2446.1	Standard non polar	33892256
D-Glutamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2504.4	Standard polar	33892256
D-Glutamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2559.7	Semi standard non polar	33892256
D-Glutamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2410.7	Standard non polar	33892256
D-Glutamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2431.4	Standard polar	33892256
D-Glutamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2584.6	Semi standard non polar	33892256
D-Glutamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2406.2	Standard non polar	33892256
D-Glutamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2413.1	Standard polar	33892256
D-Glutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2720.3	Semi standard non polar	33892256
D-Glutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2624.4	Standard non polar	33892256
D-Glutamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2380.5	Standard polar	33892256
D-Glutamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2777.9	Semi standard non polar	33892256
D-Glutamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2619.2	Standard non polar	33892256
D-Glutamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2396.9	Standard polar	33892256
D-Glutamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2866.6	Semi standard non polar	33892256
D-Glutamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2693.9	Standard non polar	33892256
D-Glutamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2429.0	Standard polar	33892256
D-Glutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3062.8	Semi standard non polar	33892256
D-Glutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2883.4	Standard non polar	33892256
D-Glutamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2422.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - D-Glutamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Glutamine EI-B (Non-derivatized)	splash10-0a4i-0920000000-c34d6fc3a22bb5865f8f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Glutamine GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glutamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-716b1947d48f42862cdf	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glutamine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9610000000-bfd7aa529a6e7f62de43	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glutamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-3900000000-3046f77d887200780992	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-72d0df6d3d9a6e78d3a8	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-470234c1ecc768038678	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-001i-0900000000-51bf3e28fa7698abc6f9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-001i-9500000000-3796f4ab6574acc38758	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-001i-9000000000-dca2e8c3ca148a6898ac	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-001i-9000000000-2d7676aa0333d3a585d6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-053r-9000000000-d9b3d51db2e7a344da6b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOF	splash10-001i-0900000000-51bf3e28fa7698abc6f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOF	splash10-001i-9500000000-3796f4ab6574acc38758	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOF	splash10-001i-9000000000-2a135ed194fe5a09dd85	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOF	splash10-001i-9000000000-2d7676aa0333d3a585d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOF	splash10-053r-9000000000-d9b3d51db2e7a344da6b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 10V, Positive-QTOF	splash10-0uea-2900000000-643cfc41a048bf920ad2	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 20V, Positive-QTOF	splash10-0f89-9600000000-0714324e1e6a088f13ce	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 40V, Positive-QTOF	splash10-0a4i-9000000000-39017fe7d7b021cbeeec	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 10V, Negative-QTOF	splash10-0002-1900000000-0f27a44e1f928092e3e4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 20V, Negative-QTOF	splash10-0f95-7900000000-b45c5a70d1db35076e47	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 40V, Negative-QTOF	splash10-0006-9000000000-a8bfd864e03c73b56b35	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 10V, Negative-QTOF	splash10-004i-0900000000-0cb66f41672a11130a67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 20V, Negative-QTOF	splash10-056v-5900000000-0f3514e6ed1c9066c5a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 40V, Negative-QTOF	splash10-0006-9000000000-4e42b8ee789c4bca31fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 10V, Positive-QTOF	splash10-001i-2900000000-a6df7f10f5a6b0c3de4d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 20V, Positive-QTOF	splash10-001i-9100000000-47e7aa43cbaf1b6a9528	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glutamine 40V, Positive-QTOF	splash10-0a59-9000000000-98e16d6011265e62f2ab	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected and Quantified	11.3 +/- 14.5 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	22.8 +/- 44.0 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Thorsen G, Bergquist J: Chiral separation of amino acids in biological fluids by micellar electrokinetic chromatography with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2000 Aug 18;745(2):389-97. [PubMed:11043757 ]

Enzymes

Enzyme Details

1. Glutaminase liver isoform, mitochondrial

General function:: Involved in glutaminase activity
Specific function:: Plays an important role in the regulation of glutamine catabolism. Promotes mitochondrial respiration and increases ATP generation in cells by catalyzing the synthesis of glutamate and alpha-ketoglutarate. Increases cellular anti-oxidant function via NADH and glutathione production. May play a role in preventing tumor proliferation.
Gene Name:: GLS2
Uniprot ID:: Q9UI32
Molecular weight:: 66322.225

Reactions

D-Glutamine + Water → D-Glutamic acid + Ammonia	details

Enzyme Details

2. Glutaminase kidney isoform, mitochondrial

General function:: Involved in glutaminase activity
Specific function:: Catalyzes the first reaction in the primary pathway for the renal catabolism of glutamine. Plays a role in maintaining acid-base homeostasis. Regulates the levels of the neurotransmitter glutamate in the brain. Isoform 2 lacks catalytic activity.
Gene Name:: GLS
Uniprot ID:: O94925
Molecular weight:: 65459.525

Reactions

D-Glutamine + Water → D-Glutamic acid + Ammonia	details

Showing metabocard for D-Glutamine (HMDB0003423)

MOL for HMDB0003423 (D-Glutamine)

3D MOL for HMDB0003423 (D-Glutamine)

3D SDF for HMDB0003423 (D-Glutamine)

3D-SDF for HMDB0003423 (D-Glutamine)

PDB for HMDB0003423 (D-Glutamine)

3D PDB for HMDB0003423 (D-Glutamine)

SMILES for HMDB0003423 (D-Glutamine)

INCHI for HMDB0003423 (D-Glutamine)

Structure for HMDB0003423 (D-Glutamine)

3D Structure for HMDB0003423 (D-Glutamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions