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Identification
NameL-Valine
Accession NumberDB00161  (NUTR00060)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(2S)-2-Amino-3-methylbutanoic acidNot AvailableNot Available
(S)-ValineNot AvailableNot Available
2-Amino-3-methylbutyric acidNot AvailableNot Available
L-(+)-alpha-Aminoisovaleric acidNot AvailableNot Available
L-alpha-Amino-beta-methylbutyric acidNot AvailableNot Available
ValNot AvailableNot Available
ValineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number72-18-4
WeightAverage: 117.1463
Monoisotopic: 117.078978601
Chemical FormulaC5H11NO2
InChI KeyKZSNJWFQEVHDMF-SGAVLPGINA-N
InChI
InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/s2
IUPAC Name
(2S)-2-amino-3-methylbutanoic acid
SMILES
CC(C)[C@H](N)C(O)=O
Mass Specshow(7.74 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsAmino Fatty Acids; Enolates; Polyamines; Carboxylic Acids; Monoalkylamines
Substituentscarboxylic acid; enolate; polyamine; primary amine; amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationPromotes mental vigor, muscle coordination, and calm emotions. May also be of use in a minority of patients with hepatic encephalopathy and in some with phenylketonuria.
PharmacodynamicsL-valine is a branched-chain essential amino acid (BCAA) that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. Valine is one of three branched-chain amino acids (the others are leucine and isoleucine) that enhance energy, increase endurance, and aid in muscle tissue recovery and repair. This group also lowers elevated blood sugar levels and increases growth hormone production. Supplemental valine should always be combined with isoleucine and leucine at a respective milligram ratio of 2:1:2. It is an essential amino acid found in proteins; important for optimal growth in infants and for growth in children and nitrogen balance in adults. The lack of L-valine may influence the growth of body, cause neuropathic obstacle, anaemia. It has wide applications in the field of pharmaceutical and food industry.
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.
AbsorptionAbsorbed from the small intestine by a sodium-dependent active-transport process.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of hypoglycemia, increased mortality in ALS patients taking large doses of BCAAs.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDiseaseSMP00201
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
Propanoate MetabolismMetabolicSMP00016
Malonic AciduriaDiseaseSMP00198
Malonyl-coa decarboxylase deficiencyDiseaseSMP00502
Beta-Ketothiolase DeficiencyDiseaseSMP00173
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Isovaleric AciduriaDiseaseSMP00238
Maple Syrup Urine DiseaseDiseaseSMP00199
Methylmalonic AciduriaDiseaseSMP00200
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
3-hydroxyisobutyric aciduriaDiseaseSMP00522
Propionic AcidemiaDiseaseSMP00236
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
Isovaleric acidemiaDiseaseSMP00524
Azithromycin Action PathwayDrug actionSMP00247
Gentamicin Action PathwayDrug actionSMP00254
Streptomycin Action PathwayDrug actionSMP00259
Chloramphenicol Action PathwayDrug actionSMP00729
Roxithromycin Action PathwayDrug actionSMP00251
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Lymecycline Action PathwayDrug actionSMP00295
Lincomycin Action PathwayDrug actionSMP00728
Erythromycin Action PathwayDrug actionSMP00250
Telithromycin Action PathwayDrug actionSMP00252
Netilmicin Action PathwayDrug actionSMP00257
Tetracycline Action PathwayDrug actionSMP00294
Tigecycline Action PathwayDrug actionSMP00712
Paromomycin Action PathwayDrug actionSMP00714
Methacycline Action PathwayDrug actionSMP00727
Clindamycin Action PathwayDrug actionSMP00249
Neomycin Action PathwayDrug actionSMP00256
Doxycycline Action PathwayDrug actionSMP00291
Oxytetracycline Action PathwayDrug actionSMP00293
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Rolitetracycline Action PathwayDrug actionSMP00726
Josamycin Action PathwayDrug actionSMP00731
Clomocycline Action PathwayDrug actionSMP00262
Clarithromycin Action PathwayDrug actionSMP00248
Kanamycin Action PathwayDrug actionSMP00255
Demeclocycline Action PathwayDrug actionSMP00290
Minocycline Action PathwayDrug actionSMP00292
Troleandomycin Action PathwayDrug actionSMP00730
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9527
Blood Brain Barrier + 0.5852
Caco-2 permeable - 0.8768
P-glycoprotein substrate Non-substrate 0.7977
P-glycoprotein inhibitor I Non-inhibitor 0.9872
P-glycoprotein inhibitor II Non-inhibitor 0.9955
Renal organic cation transporter Non-inhibitor 0.9679
CYP450 2C9 substrate Non-substrate 0.8395
CYP450 2D6 substrate Non-substrate 0.873
CYP450 3A4 substrate Non-substrate 0.7576
CYP450 1A2 substrate Non-inhibitor 0.8276
CYP450 2C9 substrate Non-inhibitor 0.9523
CYP450 2D6 substrate Non-inhibitor 0.9583
CYP450 2C19 substrate Non-inhibitor 0.9722
CYP450 3A4 substrate Non-inhibitor 0.9359
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9916
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.5785
Biodegradation Ready biodegradable 0.646
Rat acute toxicity 1.4765 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9943
hERG inhibition (predictor II) Non-inhibitor 0.9795
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-valine crystal3.19USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point315 °CPhysProp
water solubility5.85E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.26HANSCH,C ET AL. (1995)
pKa2.3 (at 13 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility214.0ALOGPS
logP-2.3ALOGPS
logP-2ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.49 m3·mol-1ChemAxon
Polarizability12.19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Hiroshi Matsui, Takayasu Tsuchida, Shigeru Nakamori, “Method for producing L-valine by fermentation.” U.S. Patent US4391907, issued July, 1981.

US4391907
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00039
KEGG CompoundC00183
ChEBI16414
ChEMBLCHEMBL43068
PharmGKBPA451843
HETVAL
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/bra_0042.shtml
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Propionyl-CoA carboxylase beta chain, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Propionyl-CoA carboxylase beta chain, mitochondrial P05166 Details

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
  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
  3. Kim SN, Ryu KH, Lee EH, Kim JS, Hahn SH: Molecular analysis of PCCB gene in Korean patients with propionic acidemia. Mol Genet Metab. 2002 Nov;77(3):209-16. Pubmed

2. Branched-chain-amino-acid aminotransferase, cytosolic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Branched-chain-amino-acid aminotransferase, cytosolic P54687 Details

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
  2. 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. Pubmed
  3. 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

3. Valine--tRNA ligase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Valine--tRNA ligase P26640 Details

References:

  1. 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
  2. Laforest MJ, Delage L, Marechal-Drouard L: The T-domain of cytosolic tRNAVal, an essential determinant for mitochondrial import. FEBS Lett. 2005 Feb 14;579(5):1072-8. Pubmed

Enzymes

1. Valine--tRNA ligase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Valine--tRNA ligase P26640 Details

References:

  1. 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
  2. Laforest MJ, Delage L, Marechal-Drouard L: The T-domain of cytosolic tRNAVal, an essential determinant for mitochondrial import. FEBS Lett. 2005 Feb 14;579(5):1072-8. Pubmed

2. Propionyl-CoA carboxylase beta chain, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Propionyl-CoA carboxylase beta chain, mitochondrial P05166 Details

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
  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
  3. Kim SN, Ryu KH, Lee EH, Kim JS, Hahn SH: Molecular analysis of PCCB gene in Korean patients with propionic acidemia. Mol Genet Metab. 2002 Nov;77(3):209-16. Pubmed

3. Branched-chain-amino-acid aminotransferase, cytosolic

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Branched-chain-amino-acid aminotransferase, cytosolic P54687 Details

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
  2. 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. Pubmed
  3. 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

Transporters

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 13:49