Isoleucine

Identification

Summary

Isoleucine is an amino acid commonly found as a component of total parenteral nutrition.

Brand Names
Aminosyn II 7 %, Sulfite-free, Aminosyn-PF 7%, Clinimix 2.75/5, Clinimix E 2.75/5, Clinisol 15, Freamine 6.9, Freamine III 10, Hepatamine 8, Nephramine, Olimel, Periolimel, Plenamine, Premasol, Primene, Procalamine 3, Prosol, Travasol 10, Trophamine 10 %
Generic Name
Isoleucine
DrugBank Accession Number
DB00167
Background

An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Weight
Average: 131.1729
Monoisotopic: 131.094628665
Chemical Formula
C6H13NO2
Synonyms
  • (2S,3S)-2-Amino-3-methylpentanoic acid
  • 2-Amino-3-methylvaleric acid
  • alpha-amino-beta-methylvaleric acid
  • Ile
  • Isoleucina
  • Isoleucine
  • Isoleucinum
  • L-Isoleucine
  • α-amino-β-methylvaleric acid

Pharmacology

Indication

The branched-chain amino acids may have antihepatic encephalopathy activity in some. They may also have anticatabolic and antitardive dyskinesia activity.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

They provide ingredients for the manufacturing of other essential biochemical components in the body, some of which are utilized for the production of energy, stimulants to the upper brain and helping you to be more alert.

Mechanism of action

(Applies to Valine, Leucine and Isoleucine) 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
UShort/branched chain specific acyl-CoA dehydrogenase, mitochondrialNot AvailableHumans
UBranched-chain-amino-acid aminotransferase, cytosolicNot AvailableHumans
UBranched-chain-amino-acid aminotransferase, mitochondrialNot AvailableHumans
UIsoleucine--tRNA ligase, cytoplasmicNot AvailableHumans
UIsoleucine--tRNA ligase, mitochondrialNot AvailableHumans
Absorption

Absorbed from the small intestine by a sodium-dependent active-transport process

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of hypoglycemia, increased mortality in ALS patients taking large doses of BCAAs

Pathways
PathwayCategory
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
beta-Ketothiolase DeficiencyDisease
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Isovaleric AcidemiaDisease
Arbekacin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
3-Hydroxy-3-methylglutaryl-CoA Lyase DeficiencyDisease
Methylmalonic AciduriaDisease
Telithromycin Action PathwayDrug action
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Isobutyryl-CoA Dehydrogenase DeficiencyDisease
Tigecycline Action PathwayDrug action
Paromomycin Action PathwayDrug action
Methacycline Action PathwayDrug action
Lincomycin Action PathwayDrug action
Chloramphenicol Action PathwayDrug action
Valine, Leucine, and Isoleucine DegradationMetabolic
3-Methylglutaconic Aciduria Type IIIDisease
3-Methylglutaconic Aciduria Type IVDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseIsoleucine (150 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixIsoleucine (120 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (145 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixIsoleucine (120 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (195 mg / 100 mL) + Methionine (195 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexIsoleucine (150 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dexIsoleucine (165 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (316 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine hydrochloride (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Phenylalanine (154 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL) + Valine (159.5 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ASCE plus Derma Signal Kit SRLVIsoleucine (0.01 mg/20mg) + Isoleucine (0.0025 g/5.0mL) + Leucine (0.01 mg/20mg) + Leucine (0.0025 g/5.0mL)KitTopicalExocobio Inc.2021-10-01Not applicableUS flag
ASCE plus Derma Signal Kit SRLVIsoleucine (0.01 mg/20mg) + Isoleucine (0.0025 g/5.0mL) + Leucine (0.01 mg/20mg) + Leucine (0.0025 g/5.0mL)KitTopicalExocobio Inc.2021-10-01Not applicableUS flag
ASCE plus Derma Signal Kit SRLV SIsoleucine (0.0006 mg/20mg) + Isoleucine (0.0001 g/5.0mL) + Leucine (0.0008 mg/20mg) + Leucine (0.0002 g/5.0mL)KitTopicalExocobio Inc.2019-03-01Not applicableUS flag
ASCE plus Derma Signal Kit SRLV SIsoleucine (0.0006 mg/20mg) + Isoleucine (0.0001 g/5.0mL) + Leucine (0.0008 mg/20mg) + Leucine (0.0002 g/5.0mL)KitTopicalExocobio Inc.2019-03-01Not applicableUS flag
ClinimixIsoleucine (5.10 g/2L) + Alanine (17.60 g/2L) + Arginine (9.78 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Leucine (6.20 g/2L) + Lysine (4.93 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Phenylalanine (4.76 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tryptophan (1.53 g/2L) + Tyrosine (0.34 g/2L) + Valine (4.93 g/2L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as isoleucine and derivatives. These are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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
Isoleucine 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
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
aspartate family amino acid, proteinogenic amino acid, L-alpha-amino acid, isoleucine (CHEBI:17191) / Common amino acids (C00407) / Amino fatty acids (LMFA01100047)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
04Y7590D77
CAS number
73-32-5
InChI Key
AGPKZVBTJJNPAG-WHFBIAKZSA-N
InChI
InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
IUPAC Name
(2S,3S)-2-amino-3-methylpentanoic acid
SMILES
CC[C@H](C)[C@H](N)C(O)=O

References

Synthesis Reference

Nelli I. Zhdanova, Tatyana V. Leonova, Ljudmila F. Kozyreva, "Method of producing L-isoleucine using Brevibacterium flavum." U.S. Patent US4237228, issued February, 1962.

US4237228
General References
Not Available
Human Metabolome Database
HMDB0000172
KEGG Drug
D00065
KEGG Compound
C00407
PubChem Compound
6306
PubChem Substance
46506864
ChemSpider
6067
BindingDB
18140
RxNav
6033
ChEBI
17191
ChEMBL
CHEMBL1233584
ZINC
ZINC000003581355
PharmGKB
PA164750430
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ILE
PDRhealth
PDRhealth Drug Page
Wikipedia
Isoleucine
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCritically Ill Patients / Starvation1
4RecruitingBasic ScienceHealthy Subjects (HS) / Obesity / Type 2 Diabetes Mellitus1
4RecruitingPreventionIntestinal Obstruction / Ischemia, Mesenteric / Laparotomy1
4TerminatedSupportive CareCancer-related Malnutrition1
4TerminatedSupportive CareCritically Ill Patients1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
SolutionIntravenous10.50 g/1000ml
InjectionIntravenous0.5 g/l
InjectionIntravenous0.25 g/1000ml
Solution, concentrateIntravenous
InjectionIntravenous0.52 g/l
InjectionIntravenous11.000 g/1000ml
SolutionIntravenous18.5 g/L
InjectionIntravenous5.5 g/1000ml
KitTopical
LiquidIntravenous
TabletOral
Injection, solutionIntravenous
Injection, emulsionIntravenous
EmulsionIntravenous0.468 g
PowderTopical
LiquidTopical
InjectionIntravenous16 g/1000ml
CapsuleOral
EmulsionParenteral20.000 g
InjectionIntravenous1.6 g/l
SolutionParenteral
InjectionIntravenous0.37 g/l
Injection, solution, concentrateIntravenous
Injection, emulsionParenteral
EmulsionIntravenous0.466 g
Injection, emulsion; injection, solutionIntravenous
EmulsionParenteral
EmulsionIntravenous
Injection, solution
Injection, emulsionIntravenous4.656 g/1000ml
Injection, emulsionIntravenous6.792 g/1000ml
SolutionIntraperitoneal
Injection, solutionIntraperitoneal
LiquidHemodialysis
SolutionIntraperitoneal0.184 g/l
EmulsionIntravenous176 g/l
EmulsionIntravenous4 g
EmulsionIntravenous3 g
SolutionIntravenous
InjectionIntravenous4 g/l
InjectionIntravenous0.21 g/100ml
EmulsionIntravenous13.000 g
EmulsionParenteral42.00 g
Injection, emulsionIntravenous14 g/1000ml
InjectionIntravenous10.30 g/l
InjectionIntravenous
Granule
Prices
Unit descriptionCostUnit
L-isoleucine powder3.21USD 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)285.5 dec °CPhysProp
water solubility3.44E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.70HANSCH,C ET AL. (1995)
pKa2.37 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility114.0 mg/mLALOGPS
logP-1.7ALOGPS
logP-1.5Chemaxon
logS-0.06ALOGPS
pKa (Strongest Acidic)2.79Chemaxon
pKa (Strongest Basic)9.59Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity34.09 m3·mol-1Chemaxon
Polarizability14.11 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9677
Blood Brain Barrier+0.78
Caco-2 permeable-0.7966
P-glycoprotein substrateNon-substrate0.7385
P-glycoprotein inhibitor INon-inhibitor0.9825
P-glycoprotein inhibitor IINon-inhibitor0.9739
Renal organic cation transporterNon-inhibitor0.9696
CYP450 2C9 substrateNon-substrate0.8513
CYP450 2D6 substrateNon-substrate0.8372
CYP450 3A4 substrateNon-substrate0.7827
CYP450 1A2 substrateNon-inhibitor0.8536
CYP450 2C9 inhibitorNon-inhibitor0.8762
CYP450 2D6 inhibitorNon-inhibitor0.9
CYP450 2C19 inhibitorNon-inhibitor0.9386
CYP450 3A4 inhibitorNon-inhibitor0.9155
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.97
Ames testNon AMES toxic0.903
CarcinogenicityNon-carcinogens0.632
BiodegradationReady biodegradable0.5166
Rat acute toxicity1.5846 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9921
hERG inhibition (predictor II)Non-inhibitor0.9735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0a4i-0930000000-e78f845bb2a8d4736476
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0a4i-0910000000-de9162d149073d0e2a37
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0a4i-0920000000-599e61f8ccdb6525c7a9
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0a4i-0910000000-742e44c426c0d6c2a9ac
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-05fr-8910000000-dbb33e0f02ac2ca5fedd
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00b9-9100000000-40bc9ef43da5f18be883
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-0920000000-37690f426455ac41e2c2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0930000000-e78f845bb2a8d4736476
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-de9162d149073d0e2a37
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0920000000-599e61f8ccdb6525c7a9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-742e44c426c0d6c2a9ac
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0udi-2392000000-74cca1eb265b8e3d7f43
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fr-8910000000-dbb33e0f02ac2ca5fedd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9100000000-27891dff695c5db53796
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-43ec1890f6dbd6aea657
Mass Spectrum (Electron Ionization)MSsplash10-004r-9000000000-34d4d4cb7042da231eb4
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-9300000000-8a23b3e62231eb65f80f
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00ko-9000000000-ac7e71578d7e1d0e8ce9
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-052f-9000000000-2586d4a089921dd977ed
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-5b11521ff6a631376d2b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-3c352f229e4067fcd489
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-8a7ef48fc0c1b6f845c2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0920000000-2e11aa1c7a5defc386db
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-b63ac9cf06eda4c54a81
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-e5b0c8c6b09f541d6dbf
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-d89d16d5c2242e44ec63
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-5de583142c7bdb381c8f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-8c75bde35c4a4073ee65
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0900000000-233a9862f616afea2d17
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-001i-1900000000-375f35065b82b13e6d6e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00dl-9000000000-d0d4a9f90fe2aca74483
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-0018f47571feaf232ff8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001r-7900000000-278dc67396114be331ba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-9000000000-e26c042aa6231eeca071
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-014r-9000000000-b6c1752fd3fbccb3d1c5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-05mo-9000000000-0569c3162621252ed0a8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-052f-9000000000-3d52b5d56d3fab45276e
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-QQ , negativeLC-MS/MSsplash10-001i-0900000000-8c75bde35c4a4073ee65
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-233a9862f616afea2d17
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-1900000000-375f35065b82b13e6d6e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00dl-9000000000-48214fe4509abf8ab954
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-0018f47571feaf232ff8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001r-7900000000-278dc67396114be331ba
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9000000000-e26c042aa6231eeca071
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014r-9000000000-23ab8ed06fcf2a11b659
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05mo-9000000000-4b80020c8cb2cfef772b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052f-9000000000-3d52b5d56d3fab45276e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-3c352f229e4067fcd489
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-8a7ef48fc0c1b6f845c2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-e5b0c8c6b09f541d6dbf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-d89d16d5c2242e44ec63
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-06233d91b909a31e69f0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-b3daa62797e4d480394a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-343094a63fc52e028a16
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-b6f87530a66d998d72ae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-3eb902a69105d9e31877
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9200000000-7271e18297b21fb986dd
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-129.4252458
predicted
DarkChem Lite v0.1.0
[M-H]-127.3373271
predicted
DarkChem Standard v0.1.0
[M-H]-129.3127458
predicted
DarkChem Lite v0.1.0
[M-H]-128.3165458
predicted
DarkChem Lite v0.1.0
[M-H]-127.389885
predicted
DeepCCS 1.0 (2019)
[M+H]+129.9852458
predicted
DarkChem Lite v0.1.0
[M+H]+129.6017458
predicted
DarkChem Lite v0.1.0
[M+H]+129.8003458
predicted
DarkChem Lite v0.1.0
[M+H]+128.5690458
predicted
DarkChem Lite v0.1.0
[M+H]+131.21724
predicted
DeepCCS 1.0 (2019)
[M+Na]+129.3641458
predicted
DarkChem Lite v0.1.0
[M+Na]+129.3149458
predicted
DarkChem Lite v0.1.0
[M+Na]+129.2581458
predicted
DarkChem Lite v0.1.0
[M+Na]+128.2558458
predicted
DarkChem Lite v0.1.0
[M+Na]+140.3864
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-ch group of donors, with a flavin as acceptor
Specific Function
Has greatest activity toward short branched chain acyl-CoA derivative such as (s)-2-methylbutyryl-CoA, isobutyryl-CoA, and 2-methylhexanoyl-CoA as well as toward short straight chain acyl-CoAs such...
Gene Name
ACADSB
Uniprot ID
P45954
Uniprot Name
Short/branched chain specific acyl-CoA dehydrogenase, mitochondrial
Molecular Weight
47485.035 Da
References
  1. Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [Article]
  2. Madsen PP, Kibaek M, Roca X, Sachidanandam R, Krainer AR, Christensen E, Steiner RD, Gibson KM, Corydon TJ, Knudsen I, Wanders RJ, Ruiter JP, Gregersen N, Andresen BS: Short/branched-chain acyl-CoA dehydrogenase deficiency due to an IVS3+3A>G mutation that causes exon skipping. Hum Genet. 2006 Feb;118(6):680-90. Epub 2005 Nov 30. [Article]
  3. Korman SH: Inborn errors of isoleucine degradation: a review. Mol Genet Metab. 2006 Dec;89(4):289-99. Epub 2006 Sep 6. [Article]
Kind
Protein
Organism
Humans
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. Goto M, Miyahara I, Hayashi H, Kagamiyama H, Hirotsu K: Crystal structures of branched-chain amino acid aminotransferase complexed with glutamate and glutarate: true reaction intermediate and double substrate recognition of the enzyme. Biochemistry. 2003 Apr 8;42(13):3725-33. [Article]
  2. 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. [Article]
  3. Beck HC: Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus. FEMS Microbiol Lett. 2005 Feb 1;243(1):37-44. [Article]
  4. Thage BV, Rattray FP, Laustsen MW, Ardo Y, Barkholt V, Houlberg U: Purification and characterization of a branched-chain amino acid aminotransferase from Lactobacillus paracasei subsp. paracasei CHCC 2115. J Appl Microbiol. 2004;96(3):593-602. [Article]
  5. Madsen SM, Beck HC, Ravn P, Vrang A, Hansen AM, Israelsen H: Cloning and inactivation of a branched-chain-amino-acid aminotransferase gene from Staphylococcus carnosus and characterization of the enzyme. Appl Environ Microbiol. 2002 Aug;68(8):4007-14. [Article]
Kind
Protein
Organism
Humans
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. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Isoleucine-trna ligase activity
Specific Function
Not Available
Gene Name
IARS
Uniprot ID
P41252
Uniprot Name
Isoleucine--tRNA ligase, cytoplasmic
Molecular Weight
144496.915 Da
References
  1. Crasto CF, Forrest AK, Karoli T, March DR, Mensah L, O'Hanlon PJ, Nairn MR, Oldham MD, Yue W, Banwell MG, Easton CJ: Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207. Bioorg Med Chem. 2003 Jul 3;11(13):2687-94. [Article]
  2. Wang P, Tang Y, Tirrell DA: Incorporation of trifluoroisoleucine into proteins in vivo. J Am Chem Soc. 2003 Jun 11;125(23):6900-6. [Article]
  3. Mock ML, Michon T, van Hest JC, Tirrell DA: Stereoselective incorporation of an unsaturated isoleucine analogue into a protein expressed in E. coli. Chembiochem. 2006 Jan;7(1):83-7. [Article]
  4. Fukunaga R, Fukai S, Ishitani R, Nureki O, Yokoyama S: Crystal structures of the CP1 domain from Thermus thermophilus isoleucyl-tRNA synthetase and its complex with L-valine. J Biol Chem. 2004 Feb 27;279(9):8396-402. Epub 2003 Dec 12. [Article]
  5. Pezo V, Metzgar D, Hendrickson TL, Waas WF, Hazebrouck S, Doring V, Marliere P, Schimmel P, De Crecy-Lagard V: Artificially ambiguous genetic code confers growth yield advantage. Proc Natl Acad Sci U S A. 2004 Jun 8;101(23):8593-7. Epub 2004 May 26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Isoleucine-trna ligase activity
Specific Function
Not Available
Gene Name
IARS2
Uniprot ID
Q9NSE4
Uniprot Name
Isoleucine--tRNA ligase, mitochondrial
Molecular Weight
113790.565 Da
References
  1. Wang P, Tang Y, Tirrell DA: Incorporation of trifluoroisoleucine into proteins in vivo. J Am Chem Soc. 2003 Jun 11;125(23):6900-6. [Article]
  2. Fukunaga R, Fukai S, Ishitani R, Nureki O, Yokoyama S: Crystal structures of the CP1 domain from Thermus thermophilus isoleucyl-tRNA synthetase and its complex with L-valine. J Biol Chem. 2004 Feb 27;279(9):8396-402. Epub 2003 Dec 12. [Article]
  3. 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. [Article]
  4. Fukunaga R, Yokoyama S: Crystal structure of leucyl-tRNA synthetase from the archaeon Pyrococcus horikoshii reveals a novel editing domain orientation. J Mol Biol. 2005 Feb 11;346(1):57-71. Epub 2004 Dec 19. [Article]
  5. Fukunaga R, Yokoyama S: Structural basis for substrate recognition by the editing domain of isoleucyl-tRNA synthetase. J Mol Biol. 2006 Jun 16;359(4):901-12. Epub 2006 Apr 25. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42