Identification

Name
L-Glutamine
Accession Number
DB00130  (NUTR00026)
Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Description

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. An oral formulation of L-glutamine was approved by the FDA in July 2017 for use in sickle cell disease [5]. This oral formulation is marketed under the tradename Endari by Emmaus Medical.

Structure
Thumb
Synonyms
  • (2S)-2-amino-4-carbamoylbutanoic acid
  • (2S)-2,5-diamino-5-oxopentanoic acid
  • (S)-2,5-diamino-5-oxopentanoic acid
  • Glutamic acid 5-amide
  • Glutamic acid amide
  • Glutamine
  • L-(+)-glutamine
  • L-2-aminoglutaramic acid
  • L-glutamic acid γ-amide
  • L-Glutamin
  • L-Glutaminsäure-5-amid
  • Levoglutamide
  • Q
External IDs
Fema no. 3684 / NSC-27421
Product Ingredients
IngredientUNIICASInChI Key
Glutamine sodiumIA7707HOQ873477-31-3YWOPZILGDZKFFC-DFWYDOINSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EndariPowder, for solution5 g/1OralEmmaus Medical, Inc.2017-07-07Not applicableUs
NutreStorePowder, for solution5 g/1OralEmmaus Medical, Inc.2008-06-04Not applicableUs
International/Other Brands
Earthlink Science Glutamine Chews Chocolate (Amerifit) / Glutamine Express (Genetic Evolutionary Nutrition) / Glutamine Fuel Mega (Twinlab) / Glutamine Fuel Powder (Twinlab) / L-Glutamine Power (Champion Nutrition)
Categories
UNII
0RH81L854J
CAS number
56-85-9
Weight
Average: 146.1445
Monoisotopic: 146.069142196
Chemical Formula
C5H10N2O3
InChI Key
ZDXPYRJPNDTMRX-VKHMYHEASA-N
InChI
InChI=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
IUPAC Name
(2S)-2-amino-4-carbamoylbutanoic acid
SMILES
N[[email protected]@H](CCC(N)=O)C(O)=O

Pharmacology

Indication

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

Used to reduce the acute complications of sickle cell disease in adult and pediatric patients 5 years of age and older [FDA Label].

Structured Indications
Not Available
Pharmacodynamics

Like other amino acids, glutamine is biochemically important as a constituent of proteins. Glutamine is also crucial in nitrogen metabolism. Ammonia (formed by nitrogen fixation) is assimilated into organic compounds by converting glutamic acid to glutamine. The enzyme which accomplishes this is called glutamine synthetase. Glutamine can then be used as a nitrogen donor in the biosynthesis of many compounds, including other amino acids, purines, and pyrimidines.

L-glutamine improves nicotinamide adenine dinucleotide (NAD) redox potential [FDA Label].

Mechanism of action

Supplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed.

The exact mechanism of L-glutamine's effect on NAD redox potential is unknown but is thought to involve increased amounts of reduced glutathione made available by glutamine supplementation [FDA Label]. This improvement in redox potential reduces the amount of oxidative damage which sickle red blood cells are more susceptible to. The reduction in cellular damage is thought to reduce chronic hemolysis and vaso-occlusive events.

TargetActionsOrganism
UCTP synthase 1
antagonist
Human
UAmidophosphoribosyltransferase
product of
Human
UGlutamine synthetase
product of
Human
Absorption

Absorption is efficient and occurs by an active transport mechanism. Tmax is 30 minutes after a single dose [FDA Label]. Absorption kinetics following multiple doses has not yet been determined.

Volume of distribution

Volume of distribution is 200 mL/kg after intravenous bolus dose [FDA Label].

Protein binding
Not Available
Metabolism

Exogenous L-glutamine likely follows the same metabolic pathways as endogenous L-glutamine which is involved in the formation of glutamate, proteins, nucleotides, and amino acid sugars [FDA Label].

Route of elimination

Primarily eliminated by metabolism [FDA Label]. While L-glutamine is filtered though the glomerulus, nearly all is reabsorbed by renal tubules.

Half life

The half life of elimination is 1 h [FDA Label].

Clearance
Not Available
Toxicity

Doses of L-glutamine up to 21 grams daily appear to be well tolerated. Reported adverse reactions are mainly gastrointestinal and not common. They include constipation and bloating. There is one older report of two hypomanic patients whose manic symptoms were exacerbated following the use of 2 to 4 grams daily of L-glutamine. The symptoms resolved when the L-glutamine was stopped. These patients were not rechallenged, nor are there any other reports of this nature.

The most common adverse effects observed in clinical trials of Endari were constipation (21%), nausea (19%), headache (18%), abdominal pain (17%), cough (16%), extremity pain (13%), back pain (12%), and chest pain (12%) [FDA Label].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Sialuria or French Type SialuriaDisease
Gout or Kelley-Seegmiller SyndromeDisease
Azathioprine Action PathwayDrug action
Xanthinuria type IIDisease
Succinic semialdehyde dehydrogenase deficiencyDisease
Mercaptopurine Metabolism PathwayDrug metabolism
Ammonia RecyclingMetabolic
Urea CycleMetabolic
Canavan DiseaseDisease
Ornithine Transcarbamylase Deficiency (OTC Deficiency)Disease
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
The oncogenic action of 2-hydroxyglutarateDisease
The oncogenic action of L-2-hydroxyglutarate in HydroxygluaricaciduriaDisease
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria Disease
Pyrimidine MetabolismMetabolic
Phenylacetate MetabolismMetabolic
Adenylosuccinate Lyase DeficiencyDisease
HypoacetylaspartiaDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
ArgininemiaDisease
Adenine phosphoribosyltransferase deficiency (APRT)Disease
Mitochondrial DNA depletion syndromeDisease
Argininosuccinic AciduriaDisease
Nicotinate and Nicotinamide MetabolismMetabolic
2-Hydroxyglutric Aciduria (D And L Form)Disease
AICA-RibosiduriaDisease
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with L-Glutamine.Approved
Food Interactions
Not Available

References

Synthesis Reference

Stephen Paul, "Novel preparation of fiber, L-glutamine and a soy derivative for the purpose of enhancement of isoflavone bioavailability." U.S. Patent US20020076455, issued June 20, 2002.

US20020076455
General References
  1. Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74. [PubMed:11408280]
  2. McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2. [PubMed:1903318]
  3. Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8. [PubMed:9488531]
  4. Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. [PubMed:10483898]
  5. Endari Approval Article [Link]
External Links
Human Metabolome Database
HMDB00641
KEGG Drug
D00015
KEGG Compound
C00064
PubChem Compound
5961
PubChem Substance
46505866
ChemSpider
5746
BindingDB
18121
ChEBI
58359
ChEMBL
CHEMBL930
PharmGKB
PA10090
IUPHAR
723
Guide to Pharmacology
GtP Drug Page
HET
GLN
PDRhealth
PDRhealth Drug Page
Wikipedia
Glutamine
ATC Codes
A16AA03 — Glutamine
FDA label
Download (121 KB)
MSDS
Download (72.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionDiabetes1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentPropionic Acidemia (PA)1
1TerminatedTreatmentCritical Illness / Shock / Traumas1
1Unknown StatusTreatmentType 2 Diabetes Mellitus1
1, 2Active Not RecruitingTreatmentAdvanced Cancers / Malignant Lymphomas1
1, 2Not Yet RecruitingTreatmentMalignant Lymphomas / Malignant Neoplasms Stated as Primary Lymphoid Haematopoietic1
1, 2RecruitingTreatmentMalignant Lymphomas1
1, 2WithdrawnTreatmentMalignant Lymphomas1
2CompletedSupportive CareLeukemias / Malignant Lymphomas / Neurotoxicity / Peripheral Neuropathy / Renal Cancers / Sarcomas1
2CompletedTreatmentCoronary Heart Disease (CHD) / Rheumatic Heart Disease1
2CompletedTreatmentDiarrhea-predominant Irritable Bowel Syndrome / Irritable Bowel Syndrome (IBS)1
2CompletedTreatmentMetastatic Colorectal Cancers1
2CompletedTreatmentMuscular Dystrophy, Duchenne1
2CompletedTreatmentPeriodontitis1
2CompletedTreatmentPulmonary Hypertension (PH) / Sickle Cell Disorders / Thalassaemic disorders1
2CompletedTreatmentSickle Cell Disorders / Thalassaemic disorders2
2RecruitingSupportive CareProstate Cancer1
2RecruitingTreatmentCancer, Breast1
2RecruitingTreatmentMultiple Myeloma (MM)1
2TerminatedPreventionChemotherapeutic Agent Toxicity / Multiple Myeloma (MM) / Peripheral Neuropathy1
2TerminatedPreventionHerpes Labialis / Herpes Simplex Virus1
2TerminatedPreventionSickle Cell Disorders1
2Unknown StatusTreatmentCritical Illness / Insulin Resistance / Stress Hyperglycaemia / Traumas1
2Unknown StatusTreatmentTrauma ICU Patients1
2WithdrawnTreatmentMalignant Lymphomas1
2WithdrawnTreatmentPlasma Cell Myeloma1
2, 3CompletedPreventionNEC / Sepsis1
2, 3CompletedTreatmentHeart Failure, Unspecified1
2, 3CompletedTreatmentMuscular Dystrophy, Duchenne1
2, 3TerminatedTreatmentCritical Illness / Respiratory Insufficiency / Sepsis1
3Active Not RecruitingSupportive CareAdvanced Cancers1
3Active Not RecruitingTreatmentCancer, Breast / Peripheral Neuropathy1
3CompletedPreventionDigestive Cancers1
3CompletedTreatmentCoronary Artery Disease1
3CompletedTreatmentCritical Illness / Intestinal Permeability / Nutrition, Enteral1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3CompletedTreatmentMuscular Dystrophy, Duchenne1
3CompletedTreatmentNeoplasms, Colorectal1
3CompletedTreatmentSickle Cell Disorders / Sickle ß0-Thalassemia1
3RecruitingTreatmentCritical Illness / Infection Complication / Inflammatory Reaction / Multiple Organ Failure / Nutrition, Enteral1
3Unknown StatusTreatmentDiarrheal Disorder1
4TerminatedTreatmentICU Patients1
Not AvailableCompletedNot AvailableCitrulline / Gastro Intestinal Failure / Intra Abdominal Pressure / Organ Failure, Multiple1
Not AvailableCompletedTreatmentBloodstream Infections / Development / Marker, Biological / Nutrition / Short Bowel Syndrome (SBS)1
Not AvailableCompletedTreatmentShock, Hemorrhagic1
Not AvailableRecruitingSupportive CareMalignant Neoplasm of Stomach1
Not AvailableUnknown StatusNot AvailableGut Function1
Not AvailableUnknown StatusBasic ScienceStatin Myopathy1
Not AvailableUnknown StatusPreventionHepatic Veno-Occlusive Disease / Mucositis / Pulmonary Veno-Occlusive Disease1
Not AvailableUnknown StatusTreatmentHyperglycemias / Infant, Low Birth Weight1
Not AvailableUnknown StatusTreatmentRadiation Enteritis1
Not AvailableWithdrawnSupportive CareChildhood Malignant Fibrous Histiocytoma of Bone / Sarcomas1
Not AvailableWithdrawnTreatmentMinor burns1

Pharmacoeconomics

Manufacturers
  • Nutritional restart pharmaceutical lp
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionOral5 g/1
Prices
Unit descriptionCostUnit
L-glutamine crystals3.76USD g
Argiment packets2.43USD packet
L-glutamine 500 mg tablet0.12USD tablet
Glutamic-500 tablet0.05USD tablet
Impact glutamine liquid0.05USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5288703No1994-10-072011-10-07Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)185.5 dec °CPhysProp
water solubility4.13E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.64CHMELIK,J ET AL. (1991)
logS-0.55ADME Research, USCD
pKa2.17MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility97.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.11 m3·mol-1ChemAxon
Polarizability13.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5588
Blood Brain Barrier+0.9604
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7302
P-glycoprotein inhibitor INon-inhibitor0.964
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.961
CYP450 2C9 substrateNon-substrate0.845
CYP450 2D6 substrateNon-substrate0.8496
CYP450 3A4 substrateNon-substrate0.7544
CYP450 1A2 substrateNon-inhibitor0.9583
CYP450 2C9 inhibitorNon-inhibitor0.9741
CYP450 2D6 inhibitorNon-inhibitor0.96
CYP450 2C19 inhibitorNon-inhibitor0.9761
CYP450 3A4 inhibitorNon-inhibitor0.8936
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9932
Ames testNon AMES toxic0.7849
CarcinogenicityNon-carcinogens0.9136
BiodegradationReady biodegradable0.8854
Rat acute toxicity1.2587 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9953
hERG inhibition (predictor II)Non-inhibitor0.9828
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.65 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0a4i-0910000000-adb283bb40327f705680
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0a4i-0910000000-134e80840320dadf6ad1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-05fr-7910000000-89f87d4acc18299244f5
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a4i-0900000000-952a471cad5e5ead0a7e
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-004i-1961000000-94183211889cfe72d4ff
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0a4i-1920000000-6505cd814f3707a0feba
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-004i-0692000000-9788416fdefb051b9586
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-adb283bb40327f705680
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-134e80840320dadf6ad1
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-00dj-4921200000-5446333d9aa592da8a07
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fr-7910000000-89f87d4acc18299244f5
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-0900000000-952a471cad5e5ead0a7e
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-1961000000-94183211889cfe72d4ff
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-1920000000-6505cd814f3707a0feba
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-0692000000-9788416fdefb051b9586
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-ce2b15fe45c57a30c6bb
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ab9-1900000000-7be5eab1056d2a249ab5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-5dc2d147bea250c7b80e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fb9-0921000000-5dcbab01982f543f7925
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004j-0940000000-102c9a43b5153f06927f
Mass Spectrum (Electron Ionization)MSsplash10-001i-9000000000-bc4e294b8a3fd8c5abce
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0059-3900000000-c8f487d1a561e49327c0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-eee04836e7577e11d0d0
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a59-9000000000-54ffbe5be8d7dbede389
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-79283391c985f8286677
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-9000000000-6afbd5929b6e2371a371
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-d5bd83614703b048228e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-dc8def340a2655f9a399
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-47e3e94a4387c53e0bd6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-9000000000-c1acfa3750a90d81ce15
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0900000000-93f01bccbc98f18d4b07
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-ce03708ec9ce55cd8952
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0933201000-9339494cebedd9c39135
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0900000000-64561a4c3590d5994e37
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0900000000-fdcdd7591fb182d804e2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03dm-0030900000-66314ae704783630947a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0933100000-8798d2e46a415bb1029a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0900000000-dddea137e500a9b364cc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0900000000-a78f8e4b2d6b37917b21
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0920000000-8c6e1eb7de6f70911080
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0002-0900000000-fa42fc4bcba608992804
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-2900000000-074610880ea19a417f60
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-059x-9200000000-8b7dae54eb8325667bd7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-e115d9215eea3f0c3629
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-55b1ac62eea66274b984
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001j-0900000000-c9c71895033d66cb2bec
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-9400000000-44011159d50b9a91d4d5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-001i-9000000000-b9d835dad7e492ebf422
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9000000000-1b1dd2de183603a45a37
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a59-9000000000-37b76ad6533df1ef5c06
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-0002-0900000000-4bbc10fc268f238c4761
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-9600000000-0723ffc1b0c4b8715831
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-001i-9000000000-c4d4596c59f9d65228d8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-fa42fc4bcba608992804
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-2900000000-9ef33cba15869a882a74
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-059x-9200000000-87603100e9cb637b9f35
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-2efd9a9911917ffc0e76
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-55b1ac62eea66274b984
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-64561a4c3590d5994e37
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-fdcdd7591fb182d804e2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-dddea137e500a9b364cc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-a78f8e4b2d6b37917b21
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001j-0900000000-c9c71895033d66cb2bec
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9400000000-44011159d50b9a91d4d5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-4453ba3a8060cc6c6bdb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-1b1dd2de183603a45a37
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a59-9000000000-37b76ad6533df1ef5c06
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-001i-0900000000-2567503ac180f3cb148f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-6afbd5929b6e2371a371
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-d5bd83614703b048228e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-dc8def340a2655f9a399
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-c1acfa3750a90d81ce15
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-93f01bccbc98f18d4b07
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-ce03708ec9ce55cd8952
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9600000000-0723ffc1b0c4b8715831
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9000000000-c4d4596c59f9d65228d8
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, glutamine, glutamine family amino acid (CHEBI:18050) / Common amino acids (C00064)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ctp synthase activity
Specific Function
This enzyme is involved in the de novo synthesis of CTP, a precursor of DNA, RNA and phospholipids. Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as a sourc...
Gene Name
CTPS1
Uniprot ID
P17812
Uniprot Name
CTP synthase 1
Molecular Weight
66689.9 Da
References
  1. MacLeod TJ, Lunn FA, Bearne SL: The role of lysine residues 297 and 306 in nucleoside triphosphate regulation of E. coli CTP synthase: inactivation by 2',3'-dialdehyde ATP and mutational analyses. Biochim Biophys Acta. 2006 Feb;1764(2):199-210. Epub 2005 Dec 27. [PubMed:16427816]
  2. Taylor SD, Mirzaei F, Sharifi A, Bearne SL: Synthesis of methylene- and difluoromethylenephosphonate analogues of uridine-4-phosphate and 3-deazauridine-4-phosphate. J Org Chem. 2006 Dec 8;71(25):9420-30. [PubMed:17137369]
  3. Fijolek A, Hofer A, Thelander L: Expression, purification, characterization, and in vivo targeting of trypanosome CTP synthetase for treatment of African sleeping sickness. J Biol Chem. 2007 Apr 20;282(16):11858-65. Epub 2007 Feb 28. [PubMed:17331943]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Product of
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
PPAT
Uniprot ID
Q06203
Uniprot Name
Amidophosphoribosyltransferase
Molecular Weight
57398.52 Da
References
  1. Jiang P, Pioszak AA, Ninfa AJ: Structure-function analysis of glutamine synthetase adenylyltransferase (ATase, EC 2.7.7.49) of Escherichia coli. Biochemistry. 2007 Apr 3;46(13):4117-32. Epub 2007 Mar 14. [PubMed:17355124]
  2. Jiang P, Mayo AE, Ninfa AJ: Escherichia coli glutamine synthetase adenylyltransferase (ATase, EC 2.7.7.49): kinetic characterization of regulation by PII, PII-UMP, glutamine, and alpha-ketoglutarate. Biochemistry. 2007 Apr 3;46(13):4133-46. Epub 2007 Mar 14. [PubMed:17355125]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Product of
General Function
Manganese ion binding
Specific Function
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). E...
Gene Name
GLUL
Uniprot ID
P15104
Uniprot Name
Glutamine synthetase
Molecular Weight
42064.15 Da
References
  1. Mong JA, Blutstein T: Estradiol modulation of astrocytic form and function: implications for hormonal control of synaptic communication. Neuroscience. 2006;138(3):967-75. Epub 2005 Dec 2. [PubMed:16326016]
  2. Rose C, Felipo V: Limited capacity for ammonia removal by brain in chronic liver failure: potential role of nitric oxide. Metab Brain Dis. 2005 Dec;20(4):275-83. [PubMed:16382338]
  3. Miguel-Hidalgo JJ: Withdrawal from free-choice ethanol consumption results in increased packing density of glutamine synthetase-immunoreactive astrocytes in the prelimbic cortex of alcohol-preferring rats. Alcohol Alcohol. 2006 Jul-Aug;41(4):379-85. Epub 2006 Feb 16. [PubMed:16484281]
  4. Chatauret N, Desjardins P, Zwingmann C, Rose C, Rao KV, Butterworth RF: Direct molecular and spectroscopic evidence for increased ammonia removal capacity of skeletal muscle in acute liver failure. J Hepatol. 2006 Jun;44(6):1083-8. Epub 2006 Jan 4. [PubMed:16530878]
  5. Tan S, Evans R, Singh B: Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops. Amino Acids. 2006 Mar;30(2):195-204. Epub 2006 Mar 20. [PubMed:16547651]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Factor XIII is activated by thrombin and calcium ion to a transglutaminase that catalyzes the formation of gamma-glutamyl-epsilon-lysine cross-links between fibrin chains, thus stabilizing the fibr...
Gene Name
F13A1
Uniprot ID
P00488
Uniprot Name
Coagulation factor XIII A chain
Molecular Weight
83266.805 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Mitkevich OV, Shainoff JR, DiBello PM, Yee VC, Teller DC, Smejkal GB, Bishop PD, Kolotushkina IS, Fickenscher K, Samokhin GP: Coagulation factor XIIIa undergoes a conformational change evoked by glutamine substrate. Studies on kinetics of inhibition and binding of XIIIA by a cross-reacting antifibrinogen antibody. J Biol Chem. 1998 Jun 5;273(23):14387-91. [PubMed:9603949]
  4. Wolff C, Lai CS: Fluorescence energy transfer detects changes in fibronectin structure upon surface binding. Arch Biochem Biophys. 1989 Feb 1;268(2):536-45. [PubMed:2913946]
  5. Wolff C, Lai CS: Evidence that the two amino termini of plasma fibronectin are in close proximity: a fluorescence energy transfer study. Biochemistry. 1988 May 3;27(9):3483-7. [PubMed:3390446]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
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 ...
Gene Name
GLS
Uniprot ID
O94925
Uniprot Name
Glutaminase kidney isoform, mitochondrial
Molecular Weight
73460.56 Da
References
  1. Masson J, Darmon M, Conjard A, Chuhma N, Ropert N, Thoby-Brisson M, Foutz AS, Parrot S, Miller GM, Jorisch R, Polan J, Hamon M, Hen R, Rayport S: Mice lacking brain/kidney phosphate-activated glutaminase have impaired glutamatergic synaptic transmission, altered breathing, disorganized goal-directed behavior and die shortly after birth. J Neurosci. 2006 Apr 26;26(17):4660-71. [PubMed:16641247]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
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-ketogl...
Gene Name
GLS2
Uniprot ID
Q9UI32
Uniprot Name
Glutaminase liver isoform, mitochondrial
Molecular Weight
66322.225 Da
References
  1. Sido B, Seel C, Hochlehnert A, Breitkreutz R, Droge W: Low intestinal glutamine level and low glutaminase activity in Crohn's disease: a rational for glutamine supplementation? Dig Dis Sci. 2006 Dec;51(12):2170-9. Epub 2006 Nov 1. [PubMed:17078002]
  2. Strohmeier M, Raschle T, Mazurkiewicz J, Rippe K, Sinning I, Fitzpatrick TB, Tews I: Structure of a bacterial pyridoxal 5'-phosphate synthase complex. Proc Natl Acad Sci U S A. 2006 Dec 19;103(51):19284-9. Epub 2006 Dec 11. [PubMed:17159152]
  3. Myers RS, Amaro RE, Luthey-Schulten ZA, Davisson VJ: Reaction coupling through interdomain contacts in imidazole glycerol phosphate synthase. Biochemistry. 2005 Sep 13;44(36):11974-85. [PubMed:16142895]
  4. Benlloch M, Mena S, Ferrer P, Obrador E, Asensi M, Pellicer JA, Carretero J, Ortega A, Estrela JM: Bcl-2 and Mn-SOD antisense oligodeoxynucleotides and a glutamine-enriched diet facilitate elimination of highly resistant B16 melanoma cells by tumor necrosis factor-alpha and chemotherapy. J Biol Chem. 2006 Jan 6;281(1):69-79. Epub 2005 Nov 1. [PubMed:16263711]
  5. Campos-Sandoval JA, Lopez de la Oliva AR, Lobo C, Segura JA, Mates JM, Alonso FJ, Marquez J: Expression of functional human glutaminase in baculovirus system: affinity purification, kinetic and molecular characterization. Int J Biochem Cell Biol. 2007;39(4):765-73. Epub 2006 Dec 21. [PubMed:17267261]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins.
Gene Name
TGM2
Uniprot ID
P21980
Uniprot Name
Protein-glutamine gamma-glutamyltransferase 2
Molecular Weight
77328.21 Da
References
  1. Park SS, Kim JM, Kim DS, Kim IH, Kim SY: Transglutaminase 2 mediates polymer formation of I-kappaBalpha through C-terminal glutamine cluster. J Biol Chem. 2006 Nov 17;281(46):34965-72. Epub 2006 Sep 20. [PubMed:16987813]
  2. Keresztessy Z, Csosz E, Harsfalvi J, Csomos K, Gray J, Lightowlers RN, Lakey JH, Balajthy Z, Fesus L: Phage display selection of efficient glutamine-donor substrate peptides for transglutaminase 2. Protein Sci. 2006 Nov;15(11):2466-80. [PubMed:17075129]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins. Contributes to the formation of the cornified cell envelope of keratinocytes.
Gene Name
TGM5
Uniprot ID
O43548
Uniprot Name
Protein-glutamine gamma-glutamyltransferase 5
Molecular Weight
80777.115 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Candi E, Paradisi A, Terrinoni A, Pietroni V, Oddi S, Cadot B, Jogini V, Meiyappan M, Clardy J, Finazzi-Agro A, Melino G: Transglutaminase 5 is regulated by guanine-adenine nucleotides. Biochem J. 2004 Jul 1;381(Pt 1):313-9. [PubMed:15038793]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins.
Gene Name
TGM6
Uniprot ID
O95932
Uniprot Name
Protein-glutamine gamma-glutamyltransferase 6
Molecular Weight
79311.745 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins. Responsible for cross-linking epidermal proteins during formation of the stratum corneum.
Gene Name
TGM1
Uniprot ID
P22735
Uniprot Name
Protein-glutamine gamma-glutamyltransferase K
Molecular Weight
89786.14 Da
References
  1. Boeshans KM, Mueser TC, Ahvazi B: A three-dimensional model of the human transglutaminase 1: insights into the understanding of lamellar ichthyosis. J Mol Model. 2007 Jan;13(1):233-46. Epub 2006 Sep 23. [PubMed:17024410]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Associated with the mammalian reproductive process. Catalyzes the cross-linking of proteins and the conjugation of polyamines to specific proteins in the seminal tract.
Gene Name
TGM4
Uniprot ID
P49221
Uniprot Name
Protein-glutamine gamma-glutamyltransferase 4
Molecular Weight
77144.595 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Stenberg P, Curtis CG, Wing D, Tong YS, Credo RB, Gray A, Lorand L: Transamidase kinetics. Amide formation in the enzymic reactions of thiol esters with amines. Biochem J. 1975 Apr;147(1):155-63. [PubMed:239698]
  4. Mosher DF: Labeling of a major fibroblast surface protein (fibronectin) catalyzed by blood coagulation factor XIIa. Biochim Biophys Acta. 1977 Mar 28;491(1):205-10. [PubMed:849457]
  5. Coyne CP, Smith JE, Keeton K: Additive and synergistic pharmacologic inhibition of equine fibrinoligase (factor XIIIa*-like) biochemical activity. Am J Vet Res. 1992 Nov;53(11):2058-66. [PubMed:1361314]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transferase activity, transferring acyl groups
Specific Function
Catalyzes the calcium-dependent formation of isopeptide cross-links between glutamine and lysine residues in various proteins, as well as the conjugation of polyamines to proteins. Involved in the ...
Gene Name
TGM3
Uniprot ID
Q08188
Uniprot Name
Protein-glutamine gamma-glutamyltransferase E
Molecular Weight
76631.26 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Chen BS, Wang MR, Xu X, Cai Y, Xu ZX, Han YL, Wu M: Transglutaminase-3, an esophageal cancer-related gene. Int J Cancer. 2000 Dec 15;88(6):862-5. [PubMed:11093806]
  4. Ikura K, Yu C, Nagao M, Sasaki R, Furuyoshi S, Kawabata N: Site-directed mutation in conserved anionic regions of guinea pig liver transglutaminase. Arch Biochem Biophys. 1995 Apr 20;318(2):307-13. [PubMed:7733658]
  5. Ahvazi B, Steinert PM: A model for the reaction mechanism of the transglutaminase 3 enzyme. Exp Mol Med. 2003 Aug 31;35(4):228-42. [PubMed:14508061]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein-glutamine gamma-glutamyltransferase activity
Specific Function
Catalyzes the cross-linking of proteins and the conjugation of polyamines to proteins.
Gene Name
TGM7
Uniprot ID
Q96PF1
Uniprot Name
Protein-glutamine gamma-glutamyltransferase Z
Molecular Weight
79940.615 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyrophosphatase activity
Specific Function
Involved in the de novo synthesis of guanine nucleotides which are not only essential for DNA and RNA synthesis, but also provide GTP, which is involved in a number of cellular processes important ...
Gene Name
GMPS
Uniprot ID
P49915
Uniprot Name
GMP synthase [glutamine-hydrolyzing]
Molecular Weight
76714.79 Da
References
  1. Strohmeier M, Raschle T, Mazurkiewicz J, Rippe K, Sinning I, Fitzpatrick TB, Tews I: Structure of a bacterial pyridoxal 5'-phosphate synthase complex. Proc Natl Acad Sci U S A. 2006 Dec 19;103(51):19284-9. Epub 2006 Dec 11. [PubMed:17159152]
  2. Myers RS, Amaro RE, Luthey-Schulten ZA, Davisson VJ: Reaction coupling through interdomain contacts in imidazole glycerol phosphate synthase. Biochemistry. 2005 Sep 13;44(36):11974-85. [PubMed:16142895]
  3. Neuwirth M, Flicker K, Strohmeier M, Tews I, Macheroux P: Thermodynamic characterization of the protein-protein interaction in the heteromeric Bacillus subtilis pyridoxalphosphate synthase. Biochemistry. 2007 May 1;46(17):5131-9. Epub 2007 Apr 5. [PubMed:17408246]
  4. Nakamura A, Yao M, Chimnaronk S, Sakai N, Tanaka I: Ammonia channel couples glutaminase with transamidase reactions in GatCAB. Science. 2006 Jun 30;312(5782):1954-8. [PubMed:16809541]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Not Available
Gene Name
ASNS
Uniprot ID
P08243
Uniprot Name
Asparagine synthetase [glutamine-hydrolyzing]
Molecular Weight
64369.39 Da
References
  1. Li KK, Beeson WT 4th, Ghiviriga I, Richards NG: A convenient gHMQC-based NMR assay for investigating ammonia channeling in glutamine-dependent amidotransferases: studies of Escherichia coli asparagine synthetase B. Biochemistry. 2007 Apr 24;46(16):4840-9. Epub 2007 Mar 31. [PubMed:17397190]
  2. Al Sarraj J, Vinson C, Thiel G: Regulation of asparagine synthetase gene transcription by the basic region leucine zipper transcription factors ATF5 and CHOP. Biol Chem. 2005 Sep;386(9):873-9. [PubMed:16164412]
  3. Sheppard K, Akochy PM, Salazar JC, Soll D: The Helicobacter pylori amidotransferase GatCAB is equally efficient in glutamine-dependent transamidation of Asp-tRNAAsn and Glu-tRNAGln. J Biol Chem. 2007 Apr 20;282(16):11866-73. Epub 2007 Feb 28. [PubMed:17329242]
  4. Barsch A, Carvalho HG, Cullimore JV, Niehaus K: GC-MS based metabolite profiling implies three interdependent ways of ammonium assimilation in Medicago truncatula root nodules. J Biotechnol. 2006 Dec 15;127(1):79-83. Epub 2006 Jun 21. [PubMed:16870293]
  5. Reinert RB, Oberle LM, Wek SA, Bunpo P, Wang XP, Mileva I, Goodwin LO, Aldrich CJ, Durden DL, McNurlan MA, Wek RC, Anthony TG: Role of glutamine depletion in directing tissue-specific nutrient stress responses to L-asparaginase. J Biol Chem. 2006 Oct 20;281(42):31222-33. Epub 2006 Aug 24. [PubMed:16931516]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transaminase activity
Specific Function
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to ...
Gene Name
CCBL1
Uniprot ID
Q16773
Uniprot Name
Kynurenine--oxoglutarate transaminase 1
Molecular Weight
47874.765 Da
References
  1. Fukushima T, Mitsuhashi S, Tomiya M, Iyo M, Hashimoto K, Toyo'oka T: Determination of kynurenic acid in human serum and its correlation with the concentration of certain amino acids. Clin Chim Acta. 2007 Feb;377(1-2):174-8. Epub 2006 Sep 30. [PubMed:17112493]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Phosphoribosylformylglycinamidine synthase activity
Specific Function
Phosphoribosylformylglycinamidine synthase involved in the purines biosynthetic pathway. Catalyzes the ATP-dependent conversion of formylglycinamide ribonucleotide (FGAR) and glutamine to yield for...
Gene Name
PFAS
Uniprot ID
O15067
Uniprot Name
Phosphoribosylformylglycinamidine synthase
Molecular Weight
144733.165 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Jayaram HN, Lui MS, Plowman J, Pillwein K, Reardon MA, Elliott WL, Weber G: Oncolytic activity and mechanism of action of a novel L-cysteine derivative, L-cysteine, ethyl ester, S-(N-methylcarbamate) monohydrochloride. Cancer Chemother Pharmacol. 1990;26(2):88-92. [PubMed:2347042]
  4. Prajda N, Natsumeda Y, Ikegami T, Reardon MA, Szondy S, Hashimoto Y, Emrani J, Weber G: Enzymic programs of rat bone marrow and the impact of acivicin and tiazofurin. Biochem Pharmacol. 1988 Mar 1;37(5):875-80. [PubMed:3345200]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Translation factor activity, rna binding
Specific Function
Allows the formation of correctly charged Gln-tRNA(Gln) through the transamidation of misacylated Glu-tRNA(Gln) in the mitochondria. The reaction takes place in the presence of glutamine and ATP th...
Gene Name
GATB
Uniprot ID
O75879
Uniprot Name
Glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrial
Molecular Weight
61863.57 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glutamine-fructose-6-phosphate transaminase (isomerizing) activity
Specific Function
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name
GFPT2
Uniprot ID
O94808
Uniprot Name
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
Molecular Weight
76929.885 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Hu Y, Riesland L, Paterson AJ, Kudlow JE: Phosphorylation of mouse glutamine-fructose-6-phosphate amidotransferase 2 (GFAT2) by cAMP-dependent protein kinase increases the enzyme activity. J Biol Chem. 2004 Jul 16;279(29):29988-93. Epub 2004 May 7. [PubMed:15133036]
  4. Zitzler J, Link D, Schafer R, Liebetrau W, Kazinski M, Bonin-Debs A, Behl C, Buckel P, Brinkmann U: High-throughput functional genomics identifies genes that ameliorate toxicity due to oxidative stress in neuronal HT-22 cells: GFPT2 protects cells against peroxide. Mol Cell Proteomics. 2004 Aug;3(8):834-40. Epub 2004 Jun 4. [PubMed:15181156]
  5. DeHaven JE, Robinson KA, Nelson BA, Buse MG: A novel variant of glutamine: fructose-6-phosphate amidotransferase-1 (GFAT1) mRNA is selectively expressed in striated muscle. Diabetes. 2001 Nov;50(11):2419-24. [PubMed:11679416]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name
CAD
Uniprot ID
P27708
Uniprot Name
CAD protein
Molecular Weight
242981.73 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glutamine-trna ligase activity
Specific Function
Plays a critical role in brain development.
Gene Name
QARS
Uniprot ID
P47897
Uniprot Name
Glutamine--tRNA ligase
Molecular Weight
87797.97 Da
References
  1. Balg C, Blais SP, Bernier S, Huot JL, Couture M, Lapointe J, Chenevert R: Synthesis of beta-ketophosphonate analogs of glutamyl and glutaminyl adenylate, and selective inhibition of the corresponding bacterial aminoacyl-tRNA synthetases. Bioorg Med Chem. 2007 Jan 1;15(1):295-304. Epub 2006 Sep 29. [PubMed:17049867]
  2. Fuchs BC, Bode BP: Stressing out over survival: glutamine as an apoptotic modulator. J Surg Res. 2006 Mar;131(1):26-40. Epub 2005 Sep 8. [PubMed:16154153]
  3. Yamasaki S, Nakamura S, Terada T, Shimizu K: Mechanism of the difference in the binding affinity of E. coli tRNAGln to glutaminyl-tRNA synthetase caused by noninterface nucleotides in variable loop. Biophys J. 2007 Jan 1;92(1):192-200. Epub 2006 Oct 6. [PubMed:17028132]
  4. Uter NT, Perona JJ: Active-site assembly in glutaminyl-tRNA synthetase by tRNA-mediated induced fit. Biochemistry. 2006 Jun 6;45(22):6858-65. [PubMed:16734422]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Nad+ synthase (glutamine-hydrolyzing) activity
Specific Function
Not Available
Gene Name
NADSYN1
Uniprot ID
Q6IA69
Uniprot Name
Glutamine-dependent NAD(+) synthetase
Molecular Weight
79283.945 Da
References
  1. Wojcik M, Seidle HF, Bieganowski P, Brenner C: Glutamine-dependent NAD+ synthetase. How a two-domain, three-substrate enzyme avoids waste. J Biol Chem. 2006 Nov 3;281(44):33395-402. Epub 2006 Sep 5. [PubMed:16954203]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate...
Gene Name
SLC38A3
Uniprot ID
Q99624
Uniprot Name
Sodium-coupled neutral amino acid transporter 3
Molecular Weight
55772.405 Da
References
  1. Umapathy NS, Li W, Mysona BA, Smith SB, Ganapathy V: Expression and function of glutamine transporters SN1 (SNAT3) and SN2 (SNAT5) in retinal Muller cells. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):3980-7. [PubMed:16249471]
  2. Conti F, Melone M: The glutamine commute: lost in the tube? Neurochem Int. 2006 May-Jun;48(6-7):459-64. Epub 2006 Mar 3. [PubMed:16517023]
  3. Gajewski M, Seaver B, Esslinger CS: Design, synthesis, and biological activity of novel triazole amino acids used to probe binding interactions between ligand and neutral amino acid transport protein SN1. Bioorg Med Chem Lett. 2007 Aug 1;17(15):4163-6. Epub 2007 May 23. [PubMed:17561393]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Virus receptor activity
Specific Function
Sodium-dependent amino acids transporter that has a broad substrate specificity, with a preference for zwitterionic amino acids. It accepts as substrates all neutral amino acids, including glutamin...
Gene Name
SLC1A5
Uniprot ID
Q15758
Uniprot Name
Neutral amino acid transporter B(0)
Molecular Weight
56597.64 Da
References
  1. Bungard CI, McGivan JD: Identification of the promoter elements involved in the stimulation of ASCT2 expression by glutamine availability in HepG2 cells and the probable involvement of FXR/RXR dimers. Arch Biochem Biophys. 2005 Nov 15;443(1-2):53-9. Epub 2005 Sep 15. [PubMed:16197915]
  2. Gegelashvili M, Rodriguez-Kern A, Pirozhkova I, Zhang J, Sung L, Gegelashvili G: High-affinity glutamate transporter GLAST/EAAT1 regulates cell surface expression of glutamine/neutral amino acid transporter ASCT2 in human fetal astrocytes. Neurochem Int. 2006 May-Jun;48(6-7):611-5. Epub 2006 Mar 3. [PubMed:16516348]
  3. Oppedisano F, Pochini L, Galluccio M, Indiveri C: The glutamine/amino acid transporter (ASCT2) reconstituted in liposomes: transport mechanism, regulation by ATP and characterization of the glutamine/glutamate antiport. Biochim Biophys Acta. 2007 Feb;1768(2):291-8. Epub 2006 Sep 16. [PubMed:17046712]
  4. Dun Y, Mysona B, Itagaki S, Martin-Studdard A, Ganapathy V, Smith SB: Functional and molecular analysis of D-serine transport in retinal Muller cells. Exp Eye Res. 2007 Jan;84(1):191-9. Epub 2006 Nov 13. [PubMed:17094966]
  5. McGivan JD, Bungard CI: The transport of glutamine into mammalian cells. Front Biosci. 2007 Jan 1;12:874-82. [PubMed:17127344]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxin transporter activity
Specific Function
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when asso...
Gene Name
SLC7A8
Uniprot ID
Q9UHI5
Uniprot Name
Large neutral amino acids transporter small subunit 2
Molecular Weight
58381.12 Da
References
  1. Umapathy NS, Li W, Mysona BA, Smith SB, Ganapathy V: Expression and function of glutamine transporters SN1 (SNAT3) and SN2 (SNAT5) in retinal Muller cells. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):3980-7. [PubMed:16249471]
  2. Kirchhoff P, Dave MH, Remy C, Kosiek O, Busque SM, Dufner M, Geibel JP, Verrey F, Wagner CA: An amino acid transporter involved in gastric acid secretion. Pflugers Arch. 2006 Mar;451(6):738-48. Epub 2005 Nov 25. [PubMed:16308696]
  3. Ramadan T, Camargo SM, Herzog B, Bordin M, Pos KM, Verrey F: Recycling of aromatic amino acids via TAT1 allows efflux of neutral amino acids via LAT2-4F2hc exchanger. Pflugers Arch. 2007 Jun;454(3):507-16. Epub 2007 Feb 2. [PubMed:17273864]
  4. Broer S, Broer A, Hansen JT, Bubb WA, Balcar VJ, Nasrallah FA, Garner B, Rae C: Alanine metabolism, transport, and cycling in the brain. J Neurochem. 2007 Sep;102(6):1758-70. Epub 2007 May 14. [PubMed:17504263]
  5. Chubb S, Kingsland AL, Broer A, Broer S: Mutation of the 4F2 heavy-chain carboxy terminus causes y+ LAT2 light-chain dysfunction. Mol Membr Biol. 2006 May-Jun;23(3):255-67. [PubMed:16785209]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:33