L-Valine

Relevant Data

Food Additives Approved in the United States:

L-VALINE [show][hide]

Mainterm L-VALINE

Doc Type ASP

CAS number 72-18-4

more

General Information

Chemical name	L-Valine
CAS number	72-18-4
Flavouring type	substances
FL No.	17.028
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

Computed Descriptors

Download SDF

2D Structure
CID	6287
IUPAC Name	(2S)-2-amino-3-methylbutanoic acid
InChI	InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
InChI Key	KZSNJWFQEVHDMF-BYPYZUCNSA-N
Canonical SMILES	CC(C)C(C(=O)O)N
Molecular Formula	C5H11NO2
Wikipedia	L-Valine

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	117.148
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Complexity	90.4
CACTVS Substructure Key Fingerprint	A A A D c c B i M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A D S j B g A Q C C A B A A g A I A A C Q C A A A A A A A A A A A A I G A A A A C A B A A A A A A Q A A E E A A A A A A A A A A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	63.3
Monoisotopic Mass	117.079
Exact Mass	117.079
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	8
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.5852
Human Intestinal Absorption	HIA+	0.9527
Caco-2 Permeability	Caco2-	0.8768
P-glycoprotein Substrate	Non-substrate	0.7977
P-glycoprotein Inhibitor	Non-inhibitor	0.9872
P-glycoprotein Inhibitor	Non-inhibitor	0.9955
Renal Organic Cation Transporter	Non-inhibitor	0.9679
Distribution
Subcellular localization	Lysosome	0.6892
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8395
CYP450 2D6 Substrate	Non-substrate	0.8730
CYP450 3A4 Substrate	Non-substrate	0.7576
CYP450 1A2 Inhibitor	Non-inhibitor	0.8276
CYP450 2C9 Inhibitor	Non-inhibitor	0.9523
CYP450 2D6 Inhibitor	Non-inhibitor	0.9583
CYP450 2C19 Inhibitor	Non-inhibitor	0.9722
CYP450 3A4 Inhibitor	Non-inhibitor	0.9359
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9916
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9943
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9795
AMES Toxicity	Non AMES toxic	0.9132
Carcinogens	Non-carcinogens	0.5785
Fish Toxicity	Low FHMT	0.5055
Tetrahymena Pyriformis Toxicity	Low TPT	0.9392
Honey Bee Toxicity	Low HBT	0.5000
Biodegradation	Ready biodegradable	0.6460
Acute Oral Toxicity	III	0.6013
Carcinogenicity (Three-class)	Non-required	0.7106

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	0.4659	LogS
Caco-2 Permeability	0.4722	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.4765	LD50, mol/kg
Fish Toxicity	3.1930	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-1.1621	pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure	Absorbed from the small intestine by a sodium-dependent active-transport process.
Mechanism of Toxicity	(Applies to Valine, Leucine and Isoleucine) <br/>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. <br/>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. <br/>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.
Metabolism	Hepatic
Toxicity Values	None
Lethal Dose	None
Carcinogenicity (IARC Classification)	No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level	None
Health Effects	None
Treatment	None
Reference	Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.[12097436 ] Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.[2026685 ] Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61.[9625050 ] Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.[12297216 ] Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75.[6696735 ] Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.[15911239 ] Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24.[14992292 ] Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7.[6198473 ] Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51.[7729054 ] Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20.[12101068 ] Stickel F, Osterreicher CH, Datz C, Ferenci P, Wolfel M, Norgauer W, Kraus MR, Wrba F, Hellerbrand C, Schuppan D: Prediction of progression to cirrhosis by a glutathione S-transferase P1 polymorphism in subjects with hereditary hemochromatosis. Arch Intern Med. 2005 Sep 12;165(16):1835-40.[16157826 ] Wudy SA, Hartmann M, Solleder C, Homoki J: Determination of 17alpha-hydroxypregnenolone in human plasma by routine isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection. Steroids. 2001 Oct;66(10):759-62.[11522338 ] Szpetnar M, Pasternak K, Boguszewska A: Branched chain amino acids (BCAAs) in heart diseases (ischaemic heart disease and myocardial infarction). Ann Univ Mariae Curie Sklodowska Med. 2004;59(2):91-5.[16146056 ] Hongpaisan J: Inhibition of proliferation of contaminating fibroblasts by D-valine in cultures of smooth muscle cells from human myometrium. Cell Biol Int. 2000;24(1):1-7.[10826768 ] Deligezer U, Akisik EE, Dalay N: Homozygosity at the C677T of the MTHFR gene is associated with increased breast cancer risk in the Turkish population. In Vivo. 2005 Sep-Oct;19(5):889-93.[16097444 ] McInturff JE, Wang SJ, Machleidt T, Lin TR, Oren A, Hertz CJ, Krutzik SR, Hart S, Zeh K, Anderson DH, Gallo RL, Modlin RL, Kim J: Granulysin-derived peptides demonstrate antimicrobial and anti-inflammatory effects against Propionibacterium acnes. J Invest Dermatol. 2005 Aug;125(2):256-63.[16098035 ] Jensen PK, Jacobsen NO: Studies of D-amino acid oxidase activity in human epidermis and cultured human epidermal cells. Arch Dermatol Res. 1984;276(1):57-64.[6142701 ] Kurpad AV, Regan MM, Raj TD, Gnanou JV, Rao VN, Young VR: The daily valine requirement of healthy adult Indians determined by the 24-h indicator amino acid balance approach. Am J Clin Nutr. 2005 Aug;82(2):373-9.[16087981 ]

From T3DB

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Subclass	Amino acids, peptides, and analogues
Intermediate Tree Nodes	Amino acids and derivatives - Alpha amino acids and derivatives
Direct Parent	Valine and derivatives
Alternative Parents	Organopnictogen compounds Amino acids Monocarboxylic acids and derivatives Carboxylic acids Monoalkylamines L-alpha-amino acids Hydrocarbon derivatives Organic oxides Methyl-branched fatty acids Carbonyl compounds
Molecular Framework	Aliphatic acyclic compounds
Substituents	Valine 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 - Organic oxide - Organopnictogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Organic oxygen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

From ClassyFire

Targets

Target Details

Branched-chain-amino-acid aminotransferase, cytosolic

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
Molecular Weight:: 42965.815 Da

References

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. [17077963 ]

Target Details

Propionyl-CoA carboxylase beta chain, mitochondrial

General Function:: Propionyl-coa carboxylase activity
Gene Name:: PCCB
Uniprot ID:: P05166
Molecular Weight:: 58215.13 Da

References

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. [12409268 ]

Target Details

Valine--tRNA ligase

General Function:: Valine-trna ligase activity
Gene Name:: VARS
Uniprot ID:: P26640
Molecular Weight:: 140474.755 Da

References

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. [15710393 ]

From T3DB

Mainterm	L-VALINE
Doc Type	ASP
CAS number	72-18-4