Valine
PubChem CID: 6287
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| Compound Synonyms | L-valine, valine, 72-18-4, (S)-Valine, H-Val-OH, (2S)-2-amino-3-methylbutanoic acid, (S)-2-Amino-3-methylbutanoic acid, 2-Amino-3-methylbutyric acid, valina, (S)-2-Amino-3-methylbutyric acid, L-alpha-Amino-beta-methylbutyric acid, Valinum [Latin], Valina [Spanish], Butanoic acid, 2-amino-3-methyl-, Valine (VAN), Valinum, Valine [USAN:INN], L-valin, VALINE, L-, L(+)-alpha-Aminoisovaleric acid, (S)-alpha-Amino-beta-methylbutyric acid, Butanoic acid, 2-amino-3-methyl-, (S)-, NSC 76038, 2-Amino-3-methylbutyric acid, (S)-, 2-Amino-3-methylbutanoic acid, (S)-, val, CHEBI:16414, UNII-HG18B9YRS7, EINECS 200-773-6, HG18B9YRS7, MFCD00064220, NSC-76038, (L)-valine, 2-Amino-3-methylbutanoic acid (VAN), Valine (L-Valine), 7004-03-7, HSDB 7800, L-2-Amino-3-methylbutanoic acid, l-(+)-alpha-Aminoisovaleric acid, L-2-Aminoisovaleric Acid, (S)-alpha-Aminoisovaleric acid, Valinum (Latin), DTXSID40883233, EC 200-773-6, VALINE (II), VALINE [II], L-Val, VALINE (MART.), VALINE [MART.], valin, 2-aminoisovaleric acid, Hval, VALINE (EP MONOGRAPH), VALINE [EP MONOGRAPH], VALINE (USP MONOGRAPH), VALINE [USP MONOGRAPH], (2S)-2-amino-3-methylbutanoate, alpha-aminoisovaleric acid, 2-amino-3-methylbutanoate, Racemic valine, L-(+)-a-Aminoisovaleric acid, s-valin, L-(+)-.alpha.-Aminoisovaleric acid, L-a-Amino-b-methylbutyric acid, 3h-l-valine, (S)-a-Amino-b-methylbutyric acid, L-Valine, FCC, Valine (USP), (+)-valine, L-Valine,(S), 1t4s, L-Valine (JP18), L-Valine, 99%, VALINE [VANDF], VALINE [HSDB], VALINE [USAN], (S)-Val, L-Val-4, L-VAL-OH, VALINE [INN], VALINE [WHO-DD], VALINE [MI], 2-Amino-3-methylbutyrate, L-VALINE [FCC], L-VALINE [JAN], bmse000052, bmse000811, bmse000860, L-(+)-a-Aminoisovalerate, L-a-Amino-b-methylbutyrate, SCHEMBL8516, (S)-A-Aminoisovaleric acid, L-VALINE [USP-RS], 2-Aminoisovaleric acid,(S), CHEMBL43068, (S)-a-Amino-b-methylbutyrate, L-(+)-alpha-Aminoisovalerate, L-iso-C3H7CH(NH2)COOH, GTPL4794, (S)-2-Amino-3-methylbutyrate, (S)-2-Amino-3-methylbutanoate, L-alpha-Amino-beta-methylbutyrate, (S)-2-amino-3-methyl-Butanoate, DTXCID201022782, Pharmakon1600-01301009, HY-N0717, (S)-alpha-Amino-beta-methylbutyrate, (S)-2-amino-3-methyl-butyric acid, BDBM50463208, NSC760111, s5628, (S)-2-amino-3-methyl-Butanoic acid, L-Valine, 98.5-101.5%, AKOS015841564, CCG-266067, CS-W020706, DB00161, FV00534, L-Valine, 99%, natural, FCC, FG, NSC-760111, RP10200, NCGC00344520-01, AS-12787, L-Valine, BioUltra, >=99.5% (NT), L-Valine, SAJ special grade, >=98.5%, DB-029989, DB-234161, L-Valine, reagent grade, >=98% (HPLC), H-Val-OH, L-2-Amino-3-methylbutanoic acid, V0014, EN300-52625, C00183, D00039, L-Valine, Cell Culture Reagent (H-L-Val-OH), LYSINE ACETATE IMPURITY D [EP IMPURITY], M02950, SBI-0633454.0002, (S)-(+)-2-AMINO-3-METHYLBUTYRIC ACID, Q483752, L-Valine, certified reference material, TraceCERT(R), F8889-8698, Valine, European Pharmacopoeia (EP) Reference Standard, Z756430564, 1B39571B-0AE8-4A9A-AE80-4B898D11A981, L-Valine, dimer, meets the analytical specifications of USP, L-Valine, United States Pharmacopeia (USP) Reference Standard, L-Valine, Pharmaceutical Secondary Standard, Certified Reference Material, InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s, 200-773-6, L-Valine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 98.5-101.0% |
|---|---|
| Topological Polar Surface Area | 63.3 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | KZSNJWFQEVHDMF-BYPYZUCNSA-N |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Synonyms | (2S)-2-Amino-3-methylbutanoic acid, (S)-Valine, 2-Amino-3-methylbutyric acid, L-(+)-alpha-Aminoisovaleric acid, L-alpha-Amino-beta-methylbutyric acid, L-Valin, V, Val, VALINE, (2S)-2-Amino-3-methylbutanoate, 2-Amino-3-methylbutyrate, L-(+)-a-Aminoisovalerate, L-(+)-a-Aminoisovaleric acid, L-(+)-alpha-Aminoisovalerate, L-(+)-Α-aminoisovalerate, L-(+)-Α-aminoisovaleric acid, L-a-Amino-b-methylbutyrate, L-a-Amino-b-methylbutyric acid, L-alpha-Amino-beta-methylbutyrate, L-Α-amino-β-methylbutyrate, L-Α-amino-β-methylbutyric acid, (S)-2-Amino-3-methyl-butanoate, (S)-2-Amino-3-methyl-butanoic acid, (S)-2-Amino-3-methylbutanoate, (S)-2-Amino-3-methylbutanoic acid, (S)-2-Amino-3-methylbutyrate, (S)-2-Amino-3-methylbutyric acid, (S)-a-Amino-b-methylbutyrate, (S)-a-Amino-b-methylbutyric acid, (S)-alpha-Amino-beta-methylbutyrate, (S)-alpha-Amino-beta-methylbutyric acid, 2-Amino-3-methylbutanoate, 2-Amino-3-methylbutanoic acid, L Valine |
| Heavy Atom Count | 8.0 |
| Compound Name | Valine |
| Kingdom | Organic compounds |
| Description | L-valine, also known as (2s)-2-amino-3-methylbutanoic acid or L-(+)-alpha-aminoisovaleric acid, belongs to valine and derivatives class of compounds. Those 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. L-valine is soluble (in water) and a moderately acidic compound (based on its pKa). L-valine can be found in watermelon, which makes L-valine a potential biomarker for the consumption of this food product. L-valine can be found primarily in most biofluids, including cerebrospinal fluid (CSF), breast milk, urine, and blood, as well as in human epidermis and fibroblasts tissues. L-valine exists in all living species, ranging from bacteria to humans. In humans, L-valine is involved in several metabolic pathways, some of which include streptomycin action pathway, tetracycline action pathway, methacycline action pathway, and kanamycin action pathway. L-valine is also involved in several metabolic disorders, some of which include methylmalonic aciduria due to cobalamin-related disorders, 3-methylglutaconic aciduria type III, isovaleric aciduria, and methylmalonic aciduria. Moreover, L-valine is found to be associated with schizophrenia, alzheimer's disease, paraquat poisoning, and hypervalinemia. L-valine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Valine (abbreviated as Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it: 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. In the genetic code it is encoded by all codons starting with GU, namely GUU, GUC, GUA, and GUG (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 (DrugBank) (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 (T3DB). |
| Exact Mass | 117.079 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 117.079 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 90.4 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 117.15 |
| Database Name | fooddb_chem_all;hmdb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Uniprot Id | P05166, P21964, P54687, O15382, P26640, Q8TF71, Q5ST30 |
| Defined Atom Stereocenter Count | 1.0 |
| Iupac Name | (2S)-2-amino-3-methylbutanoic acid |
| Total Atom Stereocenter Count | 1.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Total Bond Stereocenter Count | 0.0 |
| Class | Carboxylic acids and derivatives |
| Inchi | InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 |
| Smiles | CC(C)[C@@H](C(=O)O)N |
| Xlogp | -2.3 |
| Superclass | Organic acids and derivatives |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Amino acids, peptides, and analogues |
| Taxonomy Direct Parent | Valine and derivatives |
| Molecular Formula | C5H11NO2 |
- 1. Outgoing r'ship
FOUND_INto/from Citrullus Lanatus (Plant) Rel Props:Source_db:fooddb_chem_all