DrugBank: L-Valine (DB00161)

targets (3) enzymes (3) transporters (1)

Identification

Name

L-Valine

Accession Number

DB00161 (NUTR00060)

Type

small molecule

Groups

approved, 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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

(2S)-2-Amino-3-methylbutanoic acid
(S)-2-Amino-3-methylbutanoic acid
(S)-2-Amino-3-methylbutyric acid
(S)-a-Amino-b-methylbutyric acid
(S)-Valine
2-Amino-3-methylbutanoic acid
2-Amino-3-methylbutyric acid
L-(+)-a-Aminoisovaleric acid
L-a-Amino-b-methylbutyric acid
Valine

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Dietary supplements
Essential Amino Acids
Micronutrients

CAS number

72-18-4

Weight

Average: 117.1463
Monoisotopic: 117.078978601

Chemical Formula

C₅H₁₁NO₂

InChI Key

InChIKey=KZSNJWFQEVHDMF-BYPYZUCNSA-N

InChI

InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1

Plain Text

IUPAC Name

(2S)-2-amino-3-methylbutanoic acid

SMILES

CC(C)[C@H](N)C(O)=O

Plain Text

Mass Spec

show (7.74 KB)

Taxonomy

Kingdom

Organic

Classes

Amino Acids

Substructures

Amino Acids
Hydroxy Compounds
Acetates
Aliphatic and Aryl Amines
Carboxylic Acids and Derivatives

Pharmacology

Indication

Promotes 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.

Pharmacodynamics

L-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.

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

Toxicity

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

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Not Available

Prices

Unit description	Cost	Unit
L-valine crystal	3.19 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	315 °C	PhysProp
water solubility	5.85E+004 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	-2.26	HANSCH,C ET AL. (1995)
pKa	2.3 (at 13 °C)	KORTUM,G ET AL (1961)

Predicted Properties

Property	Value	Source
water solubility	2.14e+02 g/l	ALOGPS
logP	-2.3	ALOGPS
logP	-2	ChemAxon
logS	0.26	ALOGPS
pKa (strongest acidic)	2.72	ChemAxon
pKa (strongest basic)	9.6	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	2	ChemAxon
polar surface area	63.32	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	29.49	ChemAxon
polarizability	12.19	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00039
KEGG Compound	C00183
PubChem Compound	6287
PubChem Substance	46504886
ChemSpider	6050
ChEBI	16414
ChEMBL	16414
PharmGKB	PA451843
HET	VAL
PDRhealth	http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/bra_0042.shtml

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1UE0

FDA label

Not Available

MSDS

show (72 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Propionyl-CoA carboxylase beta chain, mitochondrial Pharmacological action: unknown Organism class: human UniProt ID: P05166 Gene: PCCB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Pharmacological action: unknown Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine Organism class: human UniProt ID: P54687 Gene: BCAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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. Valyl-tRNA synthetase Pharmacological action: unknown Organism class: human UniProt ID: P26640 Gene: VARS Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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

Targets

1. Propionyl-CoA carboxylase beta chain, mitochondrial

Pharmacological action: unknown
Organism class: human
UniProt ID: P05166 Link_out

Gene: PCCB Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

Pharmacological action: unknown

Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine

Organism class: human
UniProt ID: P54687 Link_out

Gene: BCAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
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. Valyl-tRNA synthetase

Pharmacological action: unknown
Organism class: human
UniProt ID: P26640 Link_out

Gene: VARS Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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. Valyl-tRNA synthetase Actions: substrate UniProt ID: P26640 Gene: VARS Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 Actions: substrate UniProt ID: P05166 Gene: PCCB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Actions: substrate Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine UniProt ID: P54687 Gene: BCAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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

Enzymes

1. Valyl-tRNA synthetase

Actions: substrate
UniProt ID: P26640 Link_out

Gene: VARS Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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

Actions: substrate
UniProt ID: P05166 Link_out

Gene: PCCB Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

Actions: substrate

Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine

UniProt ID: P54687 Link_out

Gene: BCAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
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 Actions: inhibitor 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) UniProt ID: Q8TF71 Gene: SLC16A10 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Transporters

1. Monocarboxylate transporter 10

Actions: inhibitor

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)

UniProt ID: Q8TF71 Link_out

Gene: SLC16A10 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19