NP-MRD: Showing NP-Card for L-Valine (NP0000609)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2025-02-11 15:40:31 UTC

NP-MRD ID

NP0000609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Valine

Description

Valine (Val) or L-valine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-valine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Valine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Valine was first isolated from casein in 1901 by Hermann Emil Fischer. The name valine comes from valeric acid, which in turn is named after the plant valerian due to the presence of valine in the roots of the plant. Valine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-valine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 Mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Like other branched-chain amino acids, the catabolism of valine starts with the removal of the amino group by transamination, giving alpha-ketoisovalerate, an alpha-keto acid, which is converted to isobutyryl-CoA through oxidative decarboxylation by the branched-chain α-ketoacid dehydrogenase complex. This is further oxidised and rearranged to succinyl-CoA, which can enter the citric acid cycle. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. Valine, like other branched-chain amino acids, is associated with insulin resistance: Higher levels of valine are observed in the blood of diabetic mice, rats, and humans (PMID: 25287287 ). Mice fed a valine deprivation diet for one day have improved insulin sensitivity and feeding of a valine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822 ). In diet-induced obese and insulin resistant mice, a diet with decreased levels of valine and the other branched-chain amino acids results in reduced adiposity and improved insulin sensitivity (PMID: 29266268 ). In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly. Hypervalinemia is another example of an inborn error of metabolism involving valine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-3-methylbutanoic acid	ChEBI
(S)-Valine	ChEBI
2-Amino-3-methylbutyric acid	ChEBI
L-(+)-alpha-Aminoisovaleric acid	ChEBI
L-alpha-Amino-beta-methylbutyric acid	ChEBI
L-Valin	ChEBI
V	ChEBI
Val	ChEBI
VALINE	ChEBI
(2S)-2-Amino-3-methylbutanoate	Generator
2-Amino-3-methylbutyrate	Generator
L-(+)-a-Aminoisovalerate	Generator
L-(+)-a-Aminoisovaleric acid	Generator
L-(+)-alpha-Aminoisovalerate	Generator
L-(+)-Α-aminoisovalerate	Generator
L-(+)-Α-aminoisovaleric acid	Generator
L-a-Amino-b-methylbutyrate	Generator
L-a-Amino-b-methylbutyric acid	Generator
L-alpha-Amino-beta-methylbutyrate	Generator
L-Α-amino-β-methylbutyrate	Generator
L-Α-amino-β-methylbutyric acid	Generator
(S)-2-Amino-3-methyl-butanoate	HMDB
(S)-2-Amino-3-methyl-butanoic acid	HMDB
(S)-2-Amino-3-methylbutanoate	HMDB
(S)-2-Amino-3-methylbutanoic acid	HMDB
(S)-2-Amino-3-methylbutyrate	HMDB
(S)-2-Amino-3-methylbutyric acid	HMDB
(S)-a-Amino-b-methylbutyrate	HMDB
(S)-a-Amino-b-methylbutyric acid	HMDB
(S)-alpha-Amino-beta-methylbutyrate	HMDB
(S)-alpha-Amino-beta-methylbutyric acid	HMDB
2-Amino-3-methylbutanoate	HMDB
2-Amino-3-methylbutanoic acid	HMDB
L Valine	HMDB

Chemical Formula

C₅H₁₁NO₂

Average Mass

117.1463 Da

Monoisotopic Mass

117.07898 Da

IUPAC Name

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

Traditional Name

L-valine

CAS Registry Number

72-18-4

SMILES

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

InChI Identifier

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-02-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-07-25	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Achillea millefolium	LOTUS Database	35616633
Allium rotundum	LOTUS Database	35616633
Allium sativum	LOTUS Database	35616633
Angelica gigas	LOTUS Database	35616633
Antirrhinum majus	LOTUS Database	35616633
Arabidopsis thaliana	KNApSAcK Database	22123792
Artemia salina	LOTUS Database	35616633
Artemisia absinthium	LOTUS Database	35616633
Astragalus falcatus	LOTUS Database	35616633
Brassica napus	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Byrsonima crassifolia	LOTUS Database	35616633
Cajanus cajan	LOTUS Database	35616633
Calendula officinalis	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capsicum annuum	KNApSAcK Database	22123792
Castanea sativa	LOTUS Database	35616633
Chlamydomonas reinhardtii	LOTUS Database	35616633
Claviceps purpurea	LOTUS Database	35616633
Colchicum trigynum	LOTUS Database	35616633
Corchorus aestuans	LOTUS Database	35616633
Curcuma domestica	KNApSAcK Database	22123792
Curcuma longa	Plant	KNApSAcK
Daphnia pulex	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Euphrasia officinalis	LOTUS Database	35616633
Flammulina velutipes	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hedera hibernica	LOTUS Database	35616633
Hevea brasiliensis	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Hypholoma fasciculare	LOTUS Database	35616633
Indigofera hirsuta	LOTUS Database	35616633
Iochroma fuchsioides	LOTUS Database	35616633
Jatropha gossypifolia	LOTUS Database	35616633
Juncus roemerianus	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lunaria annua	LOTUS Database	35616633
Lupinus albus	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Morchella angusticeps	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Mycoplasmopsis bovis	LOTUS Database	35616633
Neptunea antiqua	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Onobrychis kachetica	LOTUS Database	35616633
Opuntia ficus-indica	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Passiflora incarnata	LOTUS Database	35616633
Pentaclethra macrophylla	LOTUS Database	35616633
Pinus contorta	LOTUS Database	35616633
Pinus densiflora	LOTUS Database	35616633
Pinus ponderosa	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633
Pogostemon cablin	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Psophocarpus tetragonolobus	LOTUS Database	35616633
Rhynchospora colorata	LOTUS Database	35616633
Ripariosida hermaphrodita	LOTUS Database	35616633
Salmonella enterica	LOTUS Database	35616633
Spermacoce pusilla	LOTUS Database	35616633
Stellaria media	LOTUS Database	35616633
Suaeda aegyptiaca	LOTUS Database	35616633
Swertia angustifolia	LOTUS Database	35616633
Telekia speciosa	LOTUS Database	35616633
Thymus transcaucasicus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792
Homo sapiens (Serum)	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16414 )
L-alpha-amino acid (CHEBI:16414 )
valine (CHEBI:16414 )
pyruvate family amino acid (CHEBI:16414 )
Common amino acids (C00183 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	295 - 300 °C	Not Available
Boiling Point	213.64 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	58.5 mg/mL	Not Available
LogP	-2.26	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	214 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 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.49 m³·mol⁻¹	ChemAxon
Polarizability	12.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000883

DrugBank ID

DB00161

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16414

Good Scents ID

rw1055601

References

General References

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. [PubMed:2026685 ]
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. [PubMed:12097436 ]
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. [PubMed:6696735 ]
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. [PubMed:9625050 ]
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. [PubMed:7729054 ]
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. [PubMed:6198473 ]
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. [PubMed:15911239 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
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. [PubMed:14992292 ]
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16087981 ]
Lynch CJ, Adams SH: Branched-chain amino acids in metabolic signalling and insulin resistance. Nat Rev Endocrinol. 2014 Dec;10(12):723-36. doi: 10.1038/nrendo.2014.171. Epub 2014 Oct 7. [PubMed:25287287 ]
Xiao F, Yu J, Guo Y, Deng J, Li K, Du Y, Chen S, Zhu J, Sheng H, Guo F: Effects of individual branched-chain amino acids deprivation on insulin sensitivity and glucose metabolism in mice. Metabolism. 2014 Jun;63(6):841-50. doi: 10.1016/j.metabol.2014.03.006. Epub 2014 Mar 15. [PubMed:24684822 ]
Cummings NE, Williams EM, Kasza I, Konon EN, Schaid MD, Schmidt BA, Poudel C, Sherman DS, Yu D, Arriola Apelo SI, Cottrell SE, Geiger G, Barnes ME, Wisinski JA, Fenske RJ, Matkowskyj KA, Kimple ME, Alexander CM, Merrins MJ, Lamming DW: Restoration of metabolic health by decreased consumption of branched-chain amino acids. J Physiol. 2018 Feb 15;596(4):623-645. doi: 10.1113/JP275075. Epub 2017 Dec 27. [PubMed:29266268 ]
Kane H, Gourret Baumgart J, El-Hage W, Deloyer J, Maes C, Lebas MC, Marazziti D, Thome J, Fond-Harmant L, Denis F: Opportunities and Challenges for Professionals in Psychiatry and Mental Health Care Using Digital Technologies During the COVID-19 Pandemic: Systematic Review. JMIR Hum Factors. 2022 Feb 4;9(1):e30359. doi: 10.2196/30359. [PubMed:34736224 ]

Showing NP-Card for L-Valine (NP0000609)

MOL for NP0000609 (L-Valine)

3D MOL for NP0000609 (L-Valine)

3D SDF for NP0000609 (L-Valine)

3D-SDF for NP0000609 (L-Valine)

PDB for NP0000609 (L-Valine)

3D PDB for NP0000609 (L-Valine)

SMILES for NP0000609 (L-Valine)

INCHI for NP0000609 (L-Valine)

Structure for NP0000609 (L-Valine)

3D Structure for NP0000609 (L-Valine)