1.02020-04-17 19:15:16 UTC2020-11-18 16:39:27 UTCCDB005159(S)-beta-Aminoisobutyric acid(S)-beta-Aminoisobutyric acid, also known as (S)-3-aminoisobutyrate or (S)-3-amino-isobutanoic acid, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom (S)-beta-Aminoisobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-beta-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. beta-Aminoisobutyric acid is a non-protein amino acid originating from the catabolism of thymine and valine (S)-beta-aminoisobutyric acid and oxoglutaric acid can be converted into (S)-methylmalonic acid semialdehyde and L-glutamic acid through its interaction with the enzyme 4-aminobutyrate aminotransferase, mitochondrial. beta-Aminoisobutyric acid occurs in two isomeric forms and both enantiomers of beta-aminoisobutyric acid can be detected in human urine and plasma. In humans, (S)-beta-aminoisobutyric acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. Outside of the human body, (S)-beta-Aminoisobutyric acid has been detected, but not quantified in, several different foods, such as boysenberries, swedes, millets, mugworts, and jackfruits. This could make (S)-beta-aminoisobutyric acid a potential biomarker for the consumption of these foods. In plasma, the S-enantiomer is the predominant type due to active renal reabsorption. In addition, transient high levels of beta-aminoisobutyric acid have been observed under a variety of pathological conditions such as lead poisoning, starvation, in total body irradiation, and in a number of malignancies. It has been suggested that altered homeostasis of beta-alanine underlies some of the clinical abnormalities encountered in patients with a dihydropyrimidine dehydrogenase (DPD) deficiency. DPD constitutes the first step of the pyrimidine degradation pathway, in which the pyrimidine bases uracil and thymine are catabolized to beta-alanine and the R-enantiomer of beta-aminoisobutyric acid respectively. Hence, there might be less cross-over between the valine and thymine pathway, allowing the conversion of S-methylmalonic acid semialdehyde into (S)-beta-Aminoisobutyric acid and the subsequent accumulation of (S)-beta-Aminoisobutyric acid in plasma (PMID: 14705962, 14292857, 14453202). The S-enantiomer of beta-aminoisobutyric acid is predominantly derived from the catabolism of valine. (S)-beta-Aminoisobutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.(S)-3-Amino-2-methylpropanoic acid(S)-3-Amino-isobutanoic acid(S)-3-Amino-isobutyric acidL-3-Amino-isobutanoic acidL-3-Amino-isobutyric acid(S)-3-AminoisobutyrateL-3-Aminoisobutyrate(S)-3-Aminoisobutanoate(S)-3-Amino-2-methylpropanoate(S)-beta-Aminoisobutyrate(S)-3-Amino-isobutanoate(S)-3-Amino-isobutyrateL-3-Amino-isobutanoateL-3-Amino-isobutyrate(S)-3-Aminoisobutyric acidL-3-Aminoisobutyric acid(S)-3-Aminoisobutanoic acid(S)-b-Aminoisobutyrate(S)-b-Aminoisobutyric acid(S)-Β-aminoisobutyrate(S)-Β-aminoisobutyric acid(S)-beta-Aminoisobutyric acid(+)-a-Methyl-b-alanine(+)-alpha-Methyl-beta-alanine(+)-b-Aminoisobutyric acid(+)-beta-Aminoisobutyric acid(S)-3-amino-2-Methyl-propanoate(S)-3-amino-2-Methyl-propanoic acidL-2-Methyl-b-alanineL-2-Methyl-beta-alanineL-3-amino-2-MethylpropanoateL-3-amino-2-Methylpropanoic acidL-3-amino-2-Methylpropionic acidL-b-AminoisobutyrateL-b-Aminoisobutyric acidL-beta-AminoisobutyrateL-beta-Aminoisobutyric acidS-b-AminoisobutyrateS-beta-AminoisobutyrateS-beta-Aminoisobutyric acidC4H9NO2103.12103.0633(2S)-3-amino-2-methylpropanoic acidL-β-aminoisobutyric acid4249-19-8C[C@@H](CN)C(O)=OInChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1QCHPKSFMDHPSNR-VKHMYHEASA-N belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.Beta amino acids and derivativesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAliphatic acyclic compoundsAmino acidsCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesMonoalkylaminesMonocarboxylic acids and derivativesOrganic oxidesOrganopnictogen compoundsAliphatic acyclic compoundAmineAmino acidBeta amino acid or derivativesCarbonyl groupCarboxylic acidHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary aliphatic aminePrimary amine3-aminoisobutyric acidAmino fatty acidsbeta-amino acidmelting_point175 - 177 °Clogp-2.97logs0.55logp-2.6pka_strongest_acidic4.17pka_strongest_basic10.32iupac(2S)-3-amino-2-methylpropanoic acidaverage_mass103.12mono_mass103.0633smilesC[C@@H](CN)C(O)=OformulaC4H9NO2inchiInChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1inchikeyQCHPKSFMDHPSNR-VKHMYHEASA-Npolar_surface_area63.32refractivity25.28polarizability10.42rotatable_bond_count2acceptor_count3donor_count2physiological_charge0formal_charge0number_of_rings0bioavailability1rule_of_fiveYesghose_filterYesveber_ruleYesmddr_like_ruleYes388543C03284FDB02287843943433094CPD-4666520Van Kuilenburg AB, Stroomer AE, Van Lenthe H, Abeling NG, Van Gennip AH: New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid? Biochem J. 2004 Apr 1;379(Pt 1):119-24. doi: 10.1042/BJ20031463.14705962KAKIMOTO Y, KANAZAWA A, SANO I: IDENTIFICATION OF D(-)-BETA-AMINOISOBUTYRIC ACID IN HUMAN LIVER. Biochim Biophys Acta. 1965 Feb 15;97:376-7. doi: 10.1016/0304-4165(65)90114-5.14292857KAKIMOTO Y, ARMSTRONG MD: The preparation and isolation of D-(-)-beta-aminoisobutyric acid. J Biol Chem. 1961 Dec;236:3283-6.14453202