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Chemical Compound Review

AC1NUTP7     2-amino-3-methyl-butanoate

Synonyms: valine anion, val(-), CHEBI:32859, 2-amino-3-methylbutanoate
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Disease relevance of valine


Psychiatry related information on valine

  • In contrast, when 5-methyltetrahydrofolate is depleted by alcohol consumption, val/val individuals may be less able to compensate, leading to potentially oncogenic alterations in DNA methylation [4].
  • Two of the SNPs (rs4680 ('val/met') and rs737865) were significantly associated with (low) extraversion and, less consistently, with (high) neuroticism, with effects confined to women [6].
  • None of the carriers of the val/val genotype without cognitive impairment at baseline developed dementia during the follow up [7].
  • We have previously found an increased physical activity but a similar 24-h energy expenditure (EE) in subjects with the val/val-55 UCP2 genotype compared to those with the ala/ala genotype which indicates that the val-55 allele is statistically associated with a higher metabolic efficiency [8].
  • The BDNF (GT)(n) marker and the val/short haplotype are associated with COMD in this sample, in accordance with the previously described neurotrophic hypothesis of depression and some previous studies of association for bipolar disorder and neuroticism [9].

High impact information on valine

  • If the lambda 1lo-phenotype is due to the gly leads to val interchange in C lambda 1, then an argument can be made that (a) the lambda 1lo-phenotype is due to inefficient induction of lambda 1lo-bearing B cells and (b) B cell triggering is dependent upon a conformational change in the Ig receptor upon interaction with antigen [10].
  • Detailed analysis of 14 cases from 5 unrelated families showed that patients ran either a short (9.1 +/- 1.1 months) or a prolonged (30.8 +/- 21.3 months) clinical course according to whether they were homozygote met/met or heterozygote met/val at codon 129 [11].
  • The adjusted odds ratio (OR) for the MTHFR variant homozygous (val/val) genotype was 0.57 [95% confidence interval (CI), 0.30-1.06] [4].
  • Several tumorigenic (benign and malignant) clones have been raised from the human epidermal cell line HaCaT after transfection with the c-Ha-ras oncogene (val 12) (P. Boukamp et al., Cancer Res., 50: 2840-2847, 1990) [12].
  • Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 --> Arg and Ile523 --> val mutation [13].

Chemical compound and disease context of valine


Biological context of valine

  • Mixed model analyses revealed a main effect of BDNF val66met genotype such that in the combined sample of patients and healthy volunteers, val/val homozygotes (N=27) had larger volumes of the hippocampal formation compared to val/met heterozygotes (N=17) [17].
  • We describe an efficient and highly enantioselective conjugate transfer hydrogenation of alpha,beta-unsaturated ketones that is catalyzed by a salt made from tert-butyl valinate and a recently introduced powerful chiral phosphoric acid catalyst (TRIP) [18].
  • We previously identified a case of human acute myelogenous leukemia (AML) in which both alleles of the p53 gene had undergone independent missense mutations (at codons 135 cys to ser and 246 met to val) [19].
  • The positive control, the plasmid LTRp53cG (val), had a point mutation in exon 5 that was detected by PCR-SSCP [20].
  • Here we show that induction of cell proliferation in primary follicular cells by a mutant human Ha-ras (val 12) expressed from a retroviral vector was absolutely dependent on the presence of serum growth factors [21].

Anatomical context of valine

  • We confirmed our findings by creating a transformed RP epithelial cell line with a temperature sensitive mutant p53 (val 135) [22].
  • To best of our knowledge, this is the first paper showing ile/val genotypes and val allele of GSTP1 to be associated with higher risk of gallbladder cancer [23].
  • Morphology of the hypophysis of the freshwater teleost rhamdia hilarii (val., 1840) [24].
  • Phe-arg-arylamidase was found only in cytoplasmic fractions whereas val-pro-argarylamidase was found in cell walls, cell membranes and cytoplasmic fraction [25].

Associations of valine with other chemical compounds

  • Children with asthma with GSTP1 val/val genotype had higher malondialdehyde and lower glutathione levels compared with other genotypes (P = .023 and P = .014, respectively) [26].
  • These various data provide convergent evidence that the COMT val allele increases risk for schizophrenia by virtue of its effect on dopamine-mediated prefrontal information processing-the first plausible mechanism for a genetic effect on normal human cognition and risk for mental illness [27].
  • The main difference between solutions was in the efflux of BCAA; particularly, val and leu efflux was turned into uptake in the BCAA group [28].
  • RESULTS: At baseline, carriers of the ala/ala genotype had a median MMSE score of 27 points (interquartile range (IQR) 21.5-29), for the ala/val genotype it was 26 points (IQR 20-29), and for the val/val genotype it was 27 points (IQR 20-28.3) (p=0.3) [7].
  • Zkrml2 shows 72% and 92% identity in its basic leucine zipper domain with mouse Krml1 and zebrafish val, respectively [29].

Gene context of valine

  • In the absence of the short 5-HTTLPR allele and in the presence of the high enzyme activity COMT val/val genotype, NS scores are higher in the presence of the DRD4 seven-repeat allele [30].
  • Also, a significant association was found between tumour stage (Tis and T2+ vs. Ta and T1) and presence of the GSTP1 val allele (adjusted OR = 2.00, CI 1.14-3.52) [31].
  • To study gene-gene interactions, a combined risk of gallbladder cancer due to ile/val or val/val were calculated in combination with null alleles of GSTM1 and GSTT1 or the *B allele of GSTM3, but there was no enhancement of risk [23].
  • A significant association was not observed between the prevalence of p16 mutations in oral tumors and tobacco use, or CYP1A1 [val] or GSTM1 (0/0) genotypes [32].
  • None of the sweeps had the rare CYP1A1 genotype val/val and only one individual had the m2/m2 genotype [33].

Analytical, diagnostic and therapeutic context of valine

  • In this cross-sectional study we investigated associations between the COMT val158met polymorphism, which results in a 60-75% difference in enzyme activity between the val (high activity = H) and the met (low activity = L) variant, and skeletal phenotypes in 246 healthy pre/early pubertal girls [34].
  • There is an excess of the val COMT allele (likelihood ratio = 4.48, P = 0.03) and a trend for an excess of the val/val COMT genotype (likelihood ratio = 4.97, P = 0.08, 2 df) in the heroin addicts compared to the HRR control group [35].
  • DESIGN: EE during bicycling was determined by indirect calorimetry at three different loads (30, 40 and 60% of VO2max in eight subjects with the val/val-55 genotype (35+/-6 y weight=76.8+/-13.6 kg, VO2max=2.79+/-0.71 l/min) and eight subjects with the ala/ala-55 genotype (37+/-3 y, weight=78.3+/-16.5 kg, VO2max=2.66+/-0.41 l/min) [8].
  • The effects of the intrarenal infusion of synthetic Asn1, val 5 angiotensin II (AII) (from 0.38 to 1 mug min-1) on the determinants of glomerular filtration have been studied [36].


  1. Catechol O-methyltransferase gene variant and birth weight predict early-onset antisocial behavior in children with attention-deficit/hyperactivity disorder. Thapar, A., Langley, K., Fowler, T., Rice, F., Turic, D., Whittinger, N., Aggleton, J., Van den Bree, M., Owen, M., O'Donovan, M. Arch. Gen. Psychiatry (2005) [Pubmed]
  2. A frequent ala 4 to val superoxide dismutase-1 mutation is associated with a rapidly progressive familial amyotrophic lateral sclerosis. Rosen, D.R., Bowling, A.C., Patterson, D., Usdin, T.B., Sapp, P., Mezey, E., McKenna-Yasek, D., O'Regan, J., Rahmani, Z., Ferrante, R.J. Hum. Mol. Genet. (1994) [Pubmed]
  3. Hemoglobin North Shore: a variant hemoglobin associated with the phenotype of beta-thalassemia. Smith, C.M., Hedlund, B., Cich, J.A., Tukey, D.P., Olson, M., Steinberg, M.H., Adams, J.G. Blood (1983) [Pubmed]
  4. A methylenetetrahydrofolate reductase polymorphism and the risk of colorectal cancer. Chen, J., Giovannucci, E., Kelsey, K., Rimm, E.B., Stampfer, M.J., Colditz, G.A., Spiegelman, D., Willett, W.C., Hunter, D.J. Cancer Res. (1996) [Pubmed]
  5. A single amino acid substitution (gly743 --> val) in the steroid-binding domain of the human androgen receptor leads to Reifenstein syndrome. Nakao, R., Yanase, T., Sakai, Y., Haji, M., Nawata, H. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  6. COMT polymorphisms and anxiety-related personality traits. Stein, M.B., Fallin, M.D., Schork, N.J., Gelernter, J. Neuropsychopharmacology (2005) [Pubmed]
  7. Thermolabile methylenetetrahydrofolate reductase gene and the risk of cognitive impairment in those over 85. Gussekloo, J., Heijmans, B.T., Slagboom, P.E., Lagaay, A.M., Knook, D.L., Westendorp, R.G. J. Neurol. Neurosurg. Psychiatr. (1999) [Pubmed]
  8. The association between the val/ala-55 polymorphism of the uncoupling protein 2 gene and exercise efficiency. Buemann, B., Schierning, B., Toubro, S., Bibby, B.M., Sørensen, T., Dalgaard, L., Pedersen, O., Astrup, A. Int. J. Obes. Relat. Metab. Disord. (2001) [Pubmed]
  9. Association study of brain-derived neurotrophic factor in adults with a history of childhood onset mood disorder. Strauss, J., Barr, C.L., George, C.J., King, N., Shaikh, S., Devlin, B., Kovacs, M., Kennedy, J.L. Am. J. Med. Genet. B Neuropsychiatr. Genet. (2004) [Pubmed]
  10. Induction of lambda 1-immunoglobulin is determined by a regulatory gene (r lambda 1) linked (or identical) to the structural (c lambda 1) gene. Epstein, R., Lehmann, K., Cohn, M. J. Exp. Med. (1983) [Pubmed]
  11. Clinical features of fatal familial insomnia: phenotypic variability in relation to a polymorphism at codon 129 of the prion protein gene. Montagna, P., Cortelli, P., Avoni, P., Tinuper, P., Plazzi, G., Gallassi, R., Portaluppi, F., Julien, J., Vital, C., Delisle, M.B., Gambetti, P., Lugaresi, E. Brain Pathol. (1998) [Pubmed]
  12. Epidermal morphogenesis and keratin expression in c-Ha-ras-transfected tumorigenic clones of the human HaCaT cell line. Breitkreutz, D., Boukamp, P., Ryle, C.M., Stark, H.J., Roop, D.R., Fusenig, N.E. Cancer Res. (1991) [Pubmed]
  13. Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 --> Arg and Ile523 --> val mutation. Wong, E., Bayly, C., Waterman, H.L., Riendeau, D., Mancini, J.A. J. Biol. Chem. (1997) [Pubmed]
  14. Association of CYP1B1 polymorphisms and breast cancer risk. De Vivo, I., Hankinson, S.E., Li, L., Colditz, G.A., Hunter, D.J. Cancer Epidemiol. Biomarkers Prev. (2002) [Pubmed]
  15. CYP1A1 and GSTM1 polymorphisms in relation to lung cancer risk in Chinese women. Yang, X.R., Wacholder, S., Xu, Z., Dean, M., Clark, V., Gold, B., Brown, L.M., Stone, B.J., Fraumeni, J.F., Caporaso, N.E. Cancer Lett. (2004) [Pubmed]
  16. GEA 857 blocks potassium channels in the membrane and, thereby, prolongs muscarinic cholinergic responses in N1E-115 neuroblastoma cells. Hedlund, B., Ogren, S.O. Pharmacol. Toxicol. (1992) [Pubmed]
  17. Brain-derived neurotrophic factor val66met polymorphism and volume of the hippocampal formation. Szeszko, P.R., Lipsky, R., Mentschel, C., Robinson, D., Gunduz-Bruce, H., Sevy, S., Ashtari, M., Napolitano, B., Bilder, R.M., Kane, J.M., Goldman, D., Malhotra, A.K. Mol. Psychiatry (2005) [Pubmed]
  18. Highly Enantioselective Transfer Hydrogenation of alpha,beta-Unsaturated Ketones. Martin, N.J., List, B. J. Am. Chem. Soc. (2006) [Pubmed]
  19. Transforming activity of mutant human p53 alleles. Slingerland, J.M., Benchimol, S. J. Cell. Physiol. (1991) [Pubmed]
  20. Screening for p53 mutations in C3H/He mouse liver tumors derived spontaneously or induced with diethylnitrosamine or phenobarbitone. Rumsby, P.C., Davies, M.J., Evans, J.G. Mol. Carcinog. (1994) [Pubmed]
  21. Effect of serum growth factors and phorbol ester on growth and survival of human thyroid epithelial cells expressing mutant ras. Bond, J., Dawson, T., Lemoine, N., Wynford-Thomas, D. Mol. Carcinog. (1992) [Pubmed]
  22. Epothilone induced cytotoxicity is dependent on p53 status in prostate cells. Ioffe, M.L., White, E., Nelson, D.A., Dvorzhinski, D., DiPaola, R.S. Prostate (2004) [Pubmed]
  23. Genetic polymorphisms in GSTM1, GSTT1, GSTP1, GSTM3 and the susceptibility to gallbladder cancer in North India. Pandey, S.N., Jain, M., Nigam, P., Choudhuri, G., Mittal, B. Biomarkers (2006) [Pubmed]
  24. Morphology of the hypophysis of the freshwater teleost rhamdia hilarii (val., 1840). Val-Sella, M.V., Fava-De-Moraes, F. Anatomischer Anzeiger. (1979) [Pubmed]
  25. Degradative enzymes of oral streptococci. Willcox, M.D., Patrikakis, M., Knox, K.W. Australian dental journal. (1995) [Pubmed]
  26. Oxidative stress and genetic and epidemiologic determinants of oxidant injury in childhood asthma. Ercan, H., Birben, E., Dizdar, E.A., Keskin, O., Karaaslan, C., Soyer, O.U., Dut, R., Sackesen, C., Besler, T., Kalayci, O. J. Allergy Clin. Immunol. (2006) [Pubmed]
  27. Prefrontal neurons and the genetics of schizophrenia. Weinberger, D.R., Egan, M.F., Bertolino, A., Callicott, J.H., Mattay, V.S., Lipska, B.K., Berman, K.F., Goldberg, T.E. Biol. Psychiatry (2001) [Pubmed]
  28. Influence of parenteral nutrition on leg nitrogen exchange in injured patients. Iapichino, G., Radrizzani, D., Bonetti, G., Colombo, A., Leoni, L., Ronzoni, G., Damia, G. Crit. Care Med. (1990) [Pubmed]
  29. Expression of Zkrml2, a homologue of the Krml1/val segmentation gene, during embryonic patterning of the zebrafish (Danio rerio). Schvarzstein, M., Kirn, A., Haffter, P., Cordes, S.P. Mech. Dev. (1999) [Pubmed]
  30. Association between tridimensional personality questionnaire (TPQ) traits and three functional polymorphisms: dopamine receptor D4 (DRD4), serotonin transporter promoter region (5-HTTLPR) and catechol O-methyltransferase (COMT). Benjamin, J., Osher, Y., Kotler, M., Gritsenko, I., Nemanov, L., Belmaker, R.H., Ebstein, R.P. Mol. Psychiatry (2000) [Pubmed]
  31. Influence of GSTM1, GSTT1, GSTP1 and NAT2 genotypes on the p53 mutational spectrum in bladder tumours. Ryk, C., Berggren, P., Kumar, R., Hemminki, K., Larsson, P., Steineck, G., Lambert, B., Hou, S.M. Int. J. Cancer (2005) [Pubmed]
  32. p53, but not p16 mutations in oral squamous cell carcinomas are associated with specific CYP1A1 and GSTM1 polymorphic genotypes and patient tobacco use. Lazarus, P., Sheikh, S.N., Ren, Q., Schantz, S.P., Stern, J.C., Richie, J.P., Park, J.Y. Carcinogenesis (1998) [Pubmed]
  33. B- and T-lymphocyte micronuclei in chimney sweeps with respect to genetic polymorphism for CYP1A1 and GST1 (class Mu). Carstensen, U., Alexandrie, A.K., Högstedt, B., Rannug, A., Bratt, I., Hagmar, L. Mutat. Res. (1993) [Pubmed]
  34. The COMT val158met polymorphism is associated with early pubertal development, height and cortical bone mass in girls. Eriksson, A.L., Suuriniemi, M., Mahonen, A., Cheng, S., Ohlsson, C. Pediatr. Res. (2005) [Pubmed]
  35. Confirmation of an excess of the high enzyme activity COMT val allele in heroin addicts in a family-based haplotype relative risk study. Horowitz, R., Kotler, M., Shufman, E., Aharoni, S., Kremer, I., Cohen, H., Ebstein, R.P. Am. J. Med. Genet. (2000) [Pubmed]
  36. Determination of glomerular intracapillary and transcapillary pressure gradients from sieving data. 3. The effects of angiotensin II. Gassée, J.P., du Bois, R., Staroukine, M., Lambert, P.P. Pflugers Arch. (1976) [Pubmed]
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