Record Information
Version1.0
Creation date2015-05-07 20:38:19 UTC
Update date2019-11-26 03:21:59 UTC
Primary IDFDB030965
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-glutamine
DescriptionL-glutamine, also known as L-2-aminoglutaramic acid or levoglutamide, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-glutamine is soluble (in water) and a moderately acidic compound (based on its pKa). L-glutamine can be found in a number of food items such as acorn, yautia, ohelo berry, and oregon yampah, which makes L-glutamine a potential biomarker for the consumption of these food products. L-glutamine can be found primarily in most biofluids, including blood, sweat, breast milk, and cerebrospinal fluid (CSF), as well as throughout most human tissues. L-glutamine exists in all living species, ranging from bacteria to humans. In humans, L-glutamine is involved in several metabolic pathways, some of which include amino sugar metabolism, the oncogenic action of 2-hydroxyglutarate, mercaptopurine metabolism pathway, and transcription/Translation. L-glutamine is also involved in several metabolic disorders, some of which include the oncogenic action of d-2-hydroxyglutarate in hydroxygluaricaciduria, tay-sachs disease, xanthinuria type I, and adenosine deaminase deficiency. Moreover, L-glutamine is found to be associated with carbamoyl Phosphate Synthetase Deficiency, epilepsy, schizophrenia, and alzheimer's disease. L-glutamine is a non-carcinogenic (not listed by IARC) potentially toxic compound. L-glutamine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance.
CAS Number56-85-9
Structure
Thumb
Synonyms
SynonymSource
(2S)-2,5-Diamino-5-oxopentanoic acidChEBI
(2S)-2-Amino-4-carbamoylbutanoic acidChEBI
(S)-2,5-Diamino-5-oxopentanoic acidChEBI
Glutamic acid 5-amideChEBI
Glutamic acid amideChEBI
GLUTAMINEChEBI
L-(+)-GlutamineChEBI
L-2-Aminoglutaramic acidChEBI
L-Glutamic acid gamma-amideChEBI
L-GlutaminChEBI
L-Glutaminsaeure-5-amidChEBI
LevoglutamideChEBI
QChEBI
EndariKegg
NutrestoreKegg
(2S)-2,5-Diamino-5-oxopentanoateGenerator
(2S)-2-Amino-4-carbamoylbutanoateGenerator
(S)-2,5-Diamino-5-oxopentanoateGenerator
Glutamate 5-amideGenerator
Glutamate amideGenerator
L-2-AminoglutaramateGenerator
L-Glutamate g-amideGenerator
L-Glutamate gamma-amideGenerator
L-Glutamate γ-amideGenerator
L-Glutamic acid g-amideGenerator
L-Glutamic acid γ-amideGenerator
2-Aminoglutaramic acidHMDB
CebrogenHMDB
gamma-GlutamineHMDB
GlavaminHMDB
GluminHMDB
L-2-Aminoglutaramidic acidHMDB
L-Glutamic acid 5-amideHMDB
L-GlutamidHMDB
L-GlutamideHMDB
LevoglutamidHMDB
LevoglutamidaHMDB
LevoglutamidumHMDB
LevoglutaminaHMDB
PolyglutamineHMDB
StimulinaHMDB
D-GlutamineHMDB
D GlutamineHMDB
L GlutamineHMDB
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
Polarizability13.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H10N2O3
IUPAC name(2S)-2-amino-4-carbamoylbutanoic acid
InChI IdentifierInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
InChI KeyZDXPYRJPNDTMRX-VKHMYHEASA-N
Isomeric SMILESN[C@@H](CCC(N)=O)C(O)=O
Average Molecular Weight146.1445
Monoisotopic Molecular Weight146.069142196
Classification
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-0910000000-adb283bb40327f705680JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-0910000000-134e80840320dadf6ad1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-05fr-7910000000-89f87d4acc18299244f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-952a471cad5e5ead0a7eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-004i-1961000000-94183211889cfe72d4ffJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1920000000-6505cd814f3707a0febaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-004i-0692000000-9788416fdefb051b9586JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-adb283bb40327f705680JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-134e80840320dadf6ad1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-00dj-4921200000-5446333d9aa592da8a07JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fr-7910000000-89f87d4acc18299244f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-0900000000-952a471cad5e5ead0a7eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1961000000-94183211889cfe72d4ffJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1920000000-6505cd814f3707a0febaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-0692000000-9788416fdefb051b9586JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-ce2b15fe45c57a30c6bbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-1900000000-7be5eab1056d2a249ab5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-5dc2d147bea250c7b80eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-0921000000-5dcbab01982f543f7925JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0940000000-102c9a43b5153f06927fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-716b1947d48f42862cdfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9610000000-bfd7aa529a6e7f62de43JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0059-3900000000-c8f487d1a561e49327c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-eee04836e7577e11d0d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-54ffbe5be8d7dbede389JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-79283391c985f8286677JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-6afbd5929b6e2371a371JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d5bd83614703b048228eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-dc8def340a2655f9a399JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-47e3e94a4387c53e0bd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-c1acfa3750a90d81ce15JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-93f01bccbc98f18d4b07JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-ce03708ec9ce55cd8952JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0933201000-9339494cebedd9c39135JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-64561a4c3590d5994e37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-fdcdd7591fb182d804e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dm-0030900000-66314ae704783630947aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0933100000-8798d2e46a415bb1029aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-dddea137e500a9b364ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-a78f8e4b2d6b37917b21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0920000000-8c6e1eb7de6f70911080JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-fa42fc4bcba608992804JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-2900000000-074610880ea19a417f60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-059x-9200000000-8b7dae54eb8325667bd7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e115d9215eea3f0c3629JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-55b1ac62eea66274b984JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001j-0900000000-c9c71895033d66cb2becJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-bc4e294b8a3fd8c5abceJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference