Identification

Name
L-Leucine
Accession Number
DB00149  (NUTR00033)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

An essential branched-chain amino acid important for hemoglobin formation. [PubChem]

Structure
Thumb
Synonyms
  • (2S)-2-Amino-4-methylpentanoic acid
  • (2S)-alpha-2-Amino-4-methylvaleric acid
  • (2S)-alpha-Leucine
  • (S)-(+)-Leucine
  • (S)-Leucine
  • 2-Amino-4-methylvaleric acid
  • L
  • L-Leucin
  • L-Leuzin
  • Leu
  • Leucine
External IDs
FEMA NO. 3297
Product Ingredients
IngredientUNIICASInChI Key
L-Leucine hydrochlorideN39KV97633760-84-9XKZZNHPZEPVUQK-JEDNCBNOSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Leucine (182.5 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + Histidine (120 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Isoleucine (150 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Serine (125 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Leucine hydrochloride (155 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + Histidine (110 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Isoleucine (120 mg) + L-Lysine hydrochloride (145 mg) + L-Methionine (145 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Leucine hydrochloride (155 mg) + Glucose (10 g) + Glycine (520 mg) + Histidine (110 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Isoleucine (120 mg) + L-Lysine hydrochloride (195 mg) + L-Methionine (195 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Leucine (182.5 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + Histidine (120 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Isoleucine (150 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Serine (125 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Leucine (201 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + Histidine (132 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Isoleucine (165 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Serine (137.5 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Leucine hydrochloride (170 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + Histidine (120.5 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Isoleucine (131.5 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Leucine hydrochloride (170 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + Histidine (120.5 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Isoleucine (131.5 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Leucine (201 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + Histidine (132 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Isoleucine (165 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Serine (137.5 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Leucine hydrochloride (263 mg) + Glucose (20 g) + Glycine (880 mg) + Histidine (186 mg) + L-Alanine (880 mg) + L-Arginine (440 mg) + L-Isoleucine (203 mg) + L-Lysine hydrochloride (246 mg) + L-Methionine (246 mg) + L-Phenylalanine hydrochloride (263 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tryptophan (76 mg) + L-Tyrosine (17 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Leucine (310 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + Histidine (204 mg) + L-Alanine (880 mg) + L-Arginine (489 mg) + L-Isoleucine (255 mg) + L-Lysine hydrochloride (246.5 mg) + L-Methionine (170 mg) + L-Phenylalanine (238 mg) + L-Proline (289 mg) + L-Threonine (178.5 mg) + L-Tryptophan (76.5 mg) + L-Tyrosine (17 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Serine (212.5 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
GMW67QNF9C
CAS number
61-90-5
Weight
Average: 131.1729
Monoisotopic: 131.094628665
Chemical Formula
C6H13NO2
InChI Key
ROHFNLRQFUQHCH-YFKPBYRVSA-N
InChI
InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-4-methylpentanoic acid
SMILES
CC(C)C[[email protected]](N)C(O)=O

Pharmacology

Indication

Indicated to assist in the prevention of the breakdown of muscle proteins that sometimes occur after trauma or severe stress.

Structured Indications
Not Available
Pharmacodynamics

An essential amino acid. (Claim) Leucine helps with the regulation of blood-sugar levels, the growth and repair of muscle tissue (such as bones, skin and muscles), growth hormone production, wound healing as well as energy regulation. It can assist to prevent the breakdown of muscle proteins that sometimes occur after trauma or severe stress. It may also be beneficial for individuals with phenylketonuria - a condition in which the body cannot metabolize the amino acid phenylalanine

Mechanism of action

This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates. The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic. There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological problems are due to poor formation of myelin in the CNS.

TargetActionsOrganism
UProbable leucine--tRNA ligase, mitochondrialNot AvailableHuman
ULeucine carboxyl methyltransferase 2Not AvailableHuman
ULeucine carboxyl methyltransferase 1Not AvailableHuman
ULeucine--tRNA ligase, cytoplasmicNot AvailableHuman
UBranched-chain-amino-acid aminotransferase, mitochondrialNot AvailableHuman
UBranched-chain-amino-acid aminotransferase, cytosolicNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Valine, Leucine and Isoleucine DegradationMetabolic
Beta-Ketothiolase DeficiencyDisease
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Leucine Stimulation on Insulin SignalingSignaling
Glutaminolysis and CancerDisease
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
Clindamycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Tigecycline Action PathwayDrug action
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Propionic AcidemiaDisease
Tobramycin Action PathwayDrug action
Arbekacin Action PathwayDrug action
Methacycline Action PathwayDrug action
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
Azithromycin Action PathwayDrug action
Telithromycin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Takayasu Tsuchida, Haruo Momose, Yoshio Hirose, "Process for producing L-leucine." U.S. Patent US3970519, issued February, 1975.

US3970519
General References
Not Available
External Links
Human Metabolome Database
HMDB00687
KEGG Drug
D00030
KEGG Compound
C00123
PubChem Compound
6106
PubChem Substance
46507163
ChemSpider
5880
BindingDB
50219348
ChEBI
57427
ChEMBL
CHEMBL291962
PharmGKB
PA450197
HET
LEU
PDRhealth
PDRhealth Drug Page
Wikipedia
Leucine
MSDS
Download (72.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
1CompletedBasic ScienceCocaine Abuse1
1, 2Active Not RecruitingTreatmentBlackfan Diamond Syndrome / Congenital Hypoplastic Anemia / DBA / Diamond Blackfan Anemia / Pure Red Cell Aplasia1
1, 2CompletedTreatmentHyperoxaluria1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2CompletedTreatmentNAFLD1
2CompletedTreatmentType 2 Diabetes Mellitus2
2Not Yet RecruitingTreatmentMetabolic Syndromes1
2RecruitingPreventionBone destruction / Cancer, Breast1
2RecruitingPreventionMuscle Wasting / Quality of Life1
2RecruitingTreatmentDiamond Blackfan Anemia1
2RecruitingTreatmentMajor Depressive Disorder (MDD)1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3RecruitingTreatmentTuberculosis, Pulmonary1
4RecruitingTreatmentCardiac Arrest / Hypothermia1
Not AvailableActive Not RecruitingTreatmentMenopause1
Not AvailableCompletedNot AvailableRespiratory Distress Syndrome, Newborn1
Not AvailableCompletedDiagnosticInsulin Resistance1
Not AvailableTerminatedNot AvailableCystic Fibrosis (CF)1
Not AvailableTerminatedBasic ScienceHealthy Volunteers1
Not AvailableUnknown StatusBasic ScienceAirway Obstruction / Smoking1
Not AvailableUnknown StatusTreatmentHyperglycemias / Infant, Low Birth Weight1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
LiquidIntravenous
Injection, solution, concentrateIntravenous
EmulsionIntravenous
InjectionIntravenous
SolutionIntravenous
Prices
Unit descriptionCostUnit
Leucine powder1.62USD each
L-leucine powder0.28USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)293 °CPhysProp
water solubility2.15E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.52HANSCH,C ET AL. (1995)
pKa2.35 (at 13 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility69.8 mg/mLALOGPS
logP-1.8ALOGPS
logP-1.6ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.17 m3·mol-1ChemAxon
Polarizability14.16 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (8.19 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0pb9-0900000000-c0176b3cef05fc597576
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0a4i-0900000000-eb7cee37b9d78694010c
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0a4i-0900000000-7033b5fdcd4216168462
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0a4i-0900000000-cd1de48a6db61eb4455e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-05fr-7900000000-e3b993b282ec2115b484
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0019-9000000000-6e468213b3429cf627bc
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-0900000000-ef06e48ca82519977a37
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0pb9-0900000000-c0176b3cef05fc597576
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-eb7cee37b9d78694010c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-7033b5fdcd4216168462
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-cd1de48a6db61eb4455e
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0udi-1391000000-5183562a14017e557e33
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fr-7900000000-e3b993b282ec2115b484
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-9100000000-05b5a7a191a32803595e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-5302e9c96e75e06e9705
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-9e70778b46864cd22996
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0019-9000000000-6e468213b3429cf627bc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-4f403c61aaa8a103c049
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-d85fcc558423654f45fd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-931937d3bdd49b3ae623
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0930000000-aa1256c9224fecacf025
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-0a72425a86f804d3a16b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-4ed8cafebf4ee4e82e6a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-3ac62b780abd90dd28b1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-eb75eb03a58512ea36df
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-c0f28e4ebdef67c5b509
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0900000000-0751a9e803a2e7715d1a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-001i-5900000000-8040fc883917239630a7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-016s-9000000000-a7f9e8d43e66dbd02b6f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001r-7900000000-da119558c426d9c9d3a1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-9000000000-ae8365105ae2a18e0c10
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000f-9000000000-228ee614be6648b37433
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0006-9000000000-d1f3e047af455e156a1e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9000000000-409dfbdb20719c3afda5
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-001i-0900000000-720554d58264a9cfdb67
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-0900000000-90fab591d1f6d6318002
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-ed843252a559d532dc5e
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/MSsplash10-001i-0900000000-c0f28e4ebdef67c5b509
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-0751a9e803a2e7715d1a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-5900000000-8040fc883917239630a7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-016s-9000000000-a7f9e8d43e66dbd02b6f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-ed843252a559d532dc5e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001r-7900000000-da119558c426d9c9d3a1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9000000000-ae8365105ae2a18e0c10
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000f-9000000000-228ee614be6648b37433
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-a4610cd110c812c4f490
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-409dfbdb20719c3afda5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-d85fcc558423654f45fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-4ed8cafebf4ee4e82e6a
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
L-alpha-amino acids / Methyl-branched fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Leucine or derivatives / Alpha-amino acid / L-alpha-amino acid / Branched fatty acid / Methyl-branched fatty acid / Fatty acid / Fatty acyl / Amino acid / Monocarboxylic acid or derivatives / Carboxylic acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, leucine, pyruvate family amino acid (CHEBI:15603) / Common amino acids (C00123)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Leucine-trna ligase activity
Specific Function
Not Available
Gene Name
LARS2
Uniprot ID
Q15031
Uniprot Name
Probable leucine--tRNA ligase, mitochondrial
Molecular Weight
101975.43 Da
References
  1. Ma JJ, Zhao MW, Wang ED: Split leucine-specific domain of leucyl-tRNA synthetase from the hyperthermophilic bacterium Aquifex aeolicus. Biochemistry. 2006 Dec 12;45(49):14809-16. [PubMed:17144674]
  2. Zhu B, Zhao MW, Eriani G, Wang ED: A present-day aminoacyl-tRNA synthetase with ancestral editing properties. RNA. 2007 Jan;13(1):15-21. Epub 2006 Nov 9. [PubMed:17095543]
  3. Vu MT, Martinis SA: A unique insert of leucyl-tRNA synthetase is required for aminoacylation and not amino acid editing. Biochemistry. 2007 May 1;46(17):5170-6. Epub 2007 Apr 4. [PubMed:17407263]
  4. Hsu JL, Rho SB, Vannella KM, Martinis SA: Functional divergence of a unique C-terminal domain of leucyl-tRNA synthetase to accommodate its splicing and aminoacylation roles. J Biol Chem. 2006 Aug 11;281(32):23075-82. Epub 2006 Jun 14. [PubMed:16774921]
  5. Lue SW, Kelley SO: A single residue in leucyl-tRNA synthetase affecting amino acid specificity and tRNA aminoacylation. Biochemistry. 2007 Apr 17;46(15):4466-72. Epub 2007 Mar 23. [PubMed:17378584]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Trna methyltransferase activity
Specific Function
Probable S-adenosyl-L-methionine-dependent methyltransferase that acts as a component of the wybutosine biosynthesis pathway. Wybutosine is a hyper modified guanosine with a tricyclic base found at...
Gene Name
LCMT2
Uniprot ID
O60294
Uniprot Name
tRNA wybutosine-synthesizing protein 4
Molecular Weight
75601.095 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
General Function
S-adenosylmethionine-dependent methyltransferase activity
Specific Function
Methylates the carboxyl group of the C-terminal leucine residue of protein phosphatase 2A catalytic subunits to form alpha-leucine ester residues.
Gene Name
LCMT1
Uniprot ID
Q9UIC8
Uniprot Name
Leucine carboxyl methyltransferase 1
Molecular Weight
38378.695 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
General Function
Leucine-trna ligase activity
Specific Function
Catalyzes the specific attachment of an amino acid to its cognate tRNA in a two step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end ...
Gene Name
LARS
Uniprot ID
Q9P2J5
Uniprot Name
Leucine--tRNA ligase, cytoplasmic
Molecular Weight
134465.155 Da
References
  1. Ma JJ, Zhao MW, Wang ED: Split leucine-specific domain of leucyl-tRNA synthetase from the hyperthermophilic bacterium Aquifex aeolicus. Biochemistry. 2006 Dec 12;45(49):14809-16. [PubMed:17144674]
  2. Karkhanis VA, Boniecki MT, Poruri K, Martinis SA: A viable amino acid editing activity in the leucyl-tRNA synthetase CP1-splicing domain is not required in the yeast mitochondria. J Biol Chem. 2006 Nov 3;281(44):33217-25. Epub 2006 Sep 6. [PubMed:16956879]
  3. Vu MT, Martinis SA: A unique insert of leucyl-tRNA synthetase is required for aminoacylation and not amino acid editing. Biochemistry. 2007 May 1;46(17):5170-6. Epub 2007 Apr 4. [PubMed:17407263]
  4. Hsu JL, Rho SB, Vannella KM, Martinis SA: Functional divergence of a unique C-terminal domain of leucyl-tRNA synthetase to accommodate its splicing and aminoacylation roles. J Biol Chem. 2006 Aug 11;281(32):23075-82. Epub 2006 Jun 14. [PubMed:16774921]
  5. Dohm JC, Vingron M, Staub E: Horizontal gene transfer in aminoacyl-tRNA synthetases including leucine-specific subtypes. J Mol Evol. 2006 Oct;63(4):437-47. Epub 2006 Sep 4. [PubMed:16955236]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name
BCAT2
Uniprot ID
O15382
Uniprot Name
Branched-chain-amino-acid aminotransferase, mitochondrial
Molecular Weight
44287.445 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. Berger BJ, English S, Chan G, Knodel MH: Methionine regeneration and aminotransferases in Bacillus subtilis, Bacillus cereus, and Bacillus anthracis. J Bacteriol. 2003 Apr;185(8):2418-31. [PubMed:12670965]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name
BCAT1
Uniprot ID
P54687
Uniprot Name
Branched-chain-amino-acid aminotransferase, cytosolic
Molecular Weight
42965.815 Da
References
  1. Chen CD, Huang TF, Lin CH, Guan HH, Hsieh YC, Lin YH, Huang YC, Liu MY, Chang WC, Chen CJ: Purification, crystallization and preliminary X-ray crystallographic analysis of branched-chain aminotransferase from Deinococcus radiodurans. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Jun 1;63(Pt 6):492-4. Epub 2007 May 5. [PubMed:17554170]
  2. Saito M, Nishimura K, Wakabayashi S, Kurihara T, Nagata Y: Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637. Amino Acids. 2007 Sep;33(3):445-9. Epub 2006 Nov 2. [PubMed:17077963]

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, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462]
  2. 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
Transporter activity
Specific Function
Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu,...
Gene Name
SLC16A2
Uniprot ID
P36021
Uniprot Name
Monocarboxylate transporter 8
Molecular Weight
59510.86 Da
References
  1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [PubMed:12871948]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:27