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Record Information
Version4.0
Creation Date2006-08-12 20:33:24 UTC
Update Date2017-09-27 08:24:21 UTC
HMDB IDHMDB0003423
Secondary Accession Numbers
  • HMDB03423
Metabolite Identification
Common NameD-Glutamine
DescriptionD-Glutamine is a non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells.
Structure
Thumb
Synonyms
ValueSource
(2R)-2,5-diamino-5-Oxopentanoic acidChEBI
(2R)-2-amino-4-Carbamoylbutanoic acidChEBI
(R)-2,5-diamino-5-Oxopentanoic acidChEBI
D-2-Aminoglutaramic acidChEBI
D-GlutaminChEBI
D-Glutaminsaeure-5-amidChEBI
DGNChEBI
(2R)-2,5-diamino-5-OxopentanoateGenerator
(2R)-2-amino-4-CarbamoylbutanoateGenerator
(R)-2,5-diamino-5-OxopentanoateGenerator
D-2-AminoglutaramateGenerator
NutrestoreHMDB
L-GlutamineMeSH
D GlutamineMeSH
L GlutamineMeSH
GlutamineMeSH
Chemical FormulaC5H10N2O3
Average Molecular Weight146.1445
Monoisotopic Molecular Weight146.069142196
IUPAC Name(2R)-2-amino-4-carbamoylbutanoic acid
Traditional NameD-glutamine
CAS Registry Number5959-95-5
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 KeyZDXPYRJPNDTMRX-GSVOUGTGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentD-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility97.8 g/LALOGPS
logP-3.3ALOGPS
logP-4ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0910000000-c753448f765ddaf37a19View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0920000000-c34d6fc3a22bb5865f8fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-c753448f765ddaf37a19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-716b1947d48f42862cdfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9610000000-bfd7aa529a6e7f62de43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-3900000000-3046f77d887200780992View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-72d0df6d3d9a6e78d3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-470234c1ecc768038678View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-51bf3e28fa7698abc6f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-9500000000-3796f4ab6574acc38758View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-dca2e8c3ca148a6898acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-2d7676aa0333d3a585d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-053r-9000000000-d9b3d51db2e7a344da6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-51bf3e28fa7698abc6f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9500000000-3796f4ab6574acc38758View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2a135ed194fe5a09dd85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2d7676aa0333d3a585d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-053r-9000000000-d9b3d51db2e7a344da6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uea-2900000000-643cfc41a048bf920ad2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9600000000-0714324e1e6a088f13ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-39017fe7d7b021cbeeecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-0f27a44e1f928092e3e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f95-7900000000-b45c5a70d1db35076e47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a8bfd864e03c73b56b35View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified11.3 +/- 14.5 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified22.8 +/- 44.0 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023171
KNApSAcK IDNot Available
Chemspider ID128633
KEGG Compound IDC00819
BioCyc IDGLUTAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6926
PubChem Compound145815
PDB IDDGN
ChEBI ID17061
References
Synthesis ReferenceQian, 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)Download (PDF)
General References
  1. 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

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 + Ammoniadetails
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 + Ammoniadetails