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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 20:33:24 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0003423
Secondary Accession Numbers
  • HMDB03423
Metabolite Identification
Common NameD-Glutamine
DescriptionD-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
Data?1582752276
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-GlutamineHMDB
D GlutamineHMDB
L GlutamineHMDB
GlutamineHMDB
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
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility97.8 g/LALOGPS
logP10(-3.3) g/LALOGPS
logP10(-4) g/LChemAxon
logS10(-0.17) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.56231661259
DarkChem[M-H]-125.36531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Glutamine,1TMS,#1C[Si](C)(C)OC(=O)[C@H](N)CCC(N)=O1579.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Glutamine,1TMS,#2C[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O1653.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Glutamine,1TMS,#3C[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O1669.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Glutamine,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)CCC(N)=O1835.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Glutamine,1TBDMS,#2CC(C)(C)[Si](C)(C)N[C@H](CCC(N)=O)C(=O)O1912.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Glutamine,1TBDMS,#3CC(C)(C)[Si](C)(C)NC(=O)CC[C@@H](N)C(=O)O1926.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Glutamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0910000000-c753448f765ddaf37a192014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Glutamine EI-B (Non-derivatized)splash10-0a4i-0920000000-c34d6fc3a22bb5865f8f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Glutamine GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-c753448f765ddaf37a192017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glutamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-716b1947d48f42862cdf2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glutamine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9610000000-bfd7aa529a6e7f62de432017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glutamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-3900000000-3046f77d8872007809922012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-72d0df6d3d9a6e78d3a82012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-470234c1ecc7680386782012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-001i-0900000000-51bf3e28fa7698abc6f92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-001i-9500000000-3796f4ab6574acc387582012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-001i-9000000000-dca2e8c3ca148a6898ac2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-001i-9000000000-2d7676aa0333d3a585d62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-053r-9000000000-d9b3d51db2e7a344da6b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-51bf3e28fa7698abc6f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOFsplash10-001i-9500000000-3796f4ab6574acc387582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-2a135ed194fe5a09dd852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-2d7676aa0333d3a585d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Glutamine LC-ESI-QQ , positive-QTOFsplash10-053r-9000000000-d9b3d51db2e7a344da6b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 10V, Positive-QTOFsplash10-0uea-2900000000-643cfc41a048bf920ad22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 20V, Positive-QTOFsplash10-0f89-9600000000-0714324e1e6a088f13ce2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 40V, Positive-QTOFsplash10-0a4i-9000000000-39017fe7d7b021cbeeec2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 10V, Negative-QTOFsplash10-0002-1900000000-0f27a44e1f928092e3e42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 20V, Negative-QTOFsplash10-0f95-7900000000-b45c5a70d1db35076e472016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 40V, Negative-QTOFsplash10-0006-9000000000-a8bfd864e03c73b56b352016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 10V, Negative-QTOFsplash10-004i-0900000000-0cb66f41672a11130a672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 20V, Negative-QTOFsplash10-056v-5900000000-0f3514e6ed1c9066c5a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 40V, Negative-QTOFsplash10-0006-9000000000-4e42b8ee789c4bca31fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 10V, Positive-QTOFsplash10-001i-2900000000-a6df7f10f5a6b0c3de4d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 20V, Positive-QTOFsplash10-001i-9100000000-47e7aa43cbaf1b6a95282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glutamine 40V, Positive-QTOFsplash10-0a59-9000000000-98e16d6011265e62f2ab2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB02174
Phenol Explorer Compound IDNot Available
FooDB IDFDB023171
KNApSAcK IDNot Available
Chemspider ID128633
KEGG Compound IDC00819
BioCyc IDGLUTAMIDE
BiGG IDNot Available
Wikipedia LinkGlutamine
METLIN ID6926
PubChem Compound145815
PDB IDNot Available
ChEBI ID17061
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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