Record Information
Version2.0
Creation Date2012-05-31 13:55:58 -0600
Update Date2015-06-03 15:54:15 -0600
Secondary Accession Numbers
  • ECMDB02166
Identification
Name:(S)-b-aminoisobutyric acid
DescriptionBeta-Aminoisobutyric acid is a non-protein amino acid originating from the catabolism of thymine and valine. Beta-Aminoisobutyric acid occurs in two isomeric forms. The S-enantiomer of beta-Aminoisobutyric acid is predominantly derived from the catabolism of valine. It has been suggested that an altered homoeostasis of b-alanine underlies some of the abnormalities with a dihydropyrimidine dehydrogenase (DPD). DPD constitutes the first step of the pyrimidine degradation pathway, in which the pyrimidine bases uracil and thymine are catabolized to b-alanine and the R-enantiomer of beta-Aminoisobutyric acid respectively. In normal situation with an intact pyrimidine degradation pathway, R-methylmalonic acid semialdehyde can be synthesized directly from the catabolism of thymine. 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. (PMID: 14705962, 14292857, 14453202)
Structure
Thumb
Synonyms:
  • (+)-a-Methyl-b-alanine
  • (+)-alpha-Methyl-beta-alanine
  • (+)-b-Aminoisobutyrate
  • (+)-b-Aminoisobutyric acid
  • (+)-beta-Aminoisobutyrate
  • (+)-beta-Aminoisobutyric acid
  • (+)-α-Methyl-β-alanine
  • (+)-β-Aminoisobutyrate
  • (+)-β-Aminoisobutyric acid
  • (S)-3-amino-2-methyl-Propanoate
  • (S)-3-amino-2-methyl-Propanoic acid
  • (S)-3-Amino-2-methylpropanoate
  • (S)-3-Amino-2-methylpropanoic acid
  • (S)-3-Amino-isobutanoate
  • (S)-3-Amino-isobutanoic acid
  • (S)-3-Amino-isobutyrate
  • (S)-3-Amino-isobutyric acid
  • (S)-b-Aminoisobutyrate
  • (S)-b-Aminoisobutyric acid
  • (S)-beta-Aminoisobutyrate
  • (S)-beta-Aminoisobutyric acid
  • (S)-β-Aminoisobutyrate
  • (S)-β-Aminoisobutyric acid
  • L-2-Methyl-b-Alanine
  • L-2-Methyl-beta-Alanine
  • L-2-Methyl-β-alanine
  • L-3-Amino-2-methylpropanoate
  • L-3-Amino-2-methylpropanoic acid
  • L-3-Amino-2-methylpropionate
  • L-3-Amino-2-methylpropionic acid
  • L-3-Amino-isobutanoate
  • L-3-Amino-isobutanoic acid
  • L-3-Amino-isobutyrate
  • L-3-Amino-isobutyric acid
  • L-b-Aminoisobutyrate
  • L-b-Aminoisobutyric acid
  • L-beta-Aminoisobutyrate
  • L-beta-Aminoisobutyric acid
  • L-β-Aminoisobutyrate
  • L-β-Aminoisobutyric acid
  • S-b-Aminoisobutyrate
  • S-b-Aminoisobutyric acid
  • S-beta-Aminoisobutyrate
  • S-beta-Aminoisobutyric acid
  • S-β-Aminoisobutyrate
  • S-β-Aminoisobutyric acid
Chemical Formula:C4H9NO2
Weight:Average: 103.1198
Monoisotopic: 103.063328537
InChI Key:QCHPKSFMDHPSNR-VKHMYHEASA-N
InChI:InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
CAS number:4249-19-8
IUPAC Name:(2S)-3-amino-2-methylpropanoic acid
Traditional IUPAC Name:L-β-aminoisobutyric acid
SMILES:C[C@@H](CN)C(O)=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:175-177 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility367 g/LALOGPS
logP-3ALOGPS
logP-2.6ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability10.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Valine, leucine and isoleucine degradation ec00280
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-59e52601f90d8e636d61View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ar-9200000000-0eb92539979a9fa36dbdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-1900000000-aaccebe5d4a868bc32bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-2900000000-4f4e49fe169d5c21efc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-4900000000-f32e82420f5efb60456eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0uk9-6900000000-cb0ef82b397e24372142View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0uk9-8900000000-31fc31847c8771693d15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0fk9-9600000000-6379643466e30660a05bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-9300000000-97e8a7125780e41fceafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-05fr-9200000000-8f0488fe62603d121536View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0ab9-9100000000-84e07fbee3e332502265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-3634b730902e2e080b56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-00di-9000000000-1b9078e3902a11473fa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-1900000000-76d19f44560e6b1b6f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-1900000000-bd4e85f35b448a2b7540View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-2900000000-b1371ec53be10ec9c411View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-3900000000-d16b3475fcdfed5038d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-4900000000-cd34930bbcb805c7525fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-5900000000-4b73ac1046680185a981View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-6900000000-a911da27982a560a6cf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-8900000000-91a255aae27e4e4aabb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9300000000-30669ed04aadf3d3f040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-ca65637476e64152c44eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-04d1648391d3f90db226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-ec54fcce079024a62344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9500000000-0394f399cdf5df93c5dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-d0c495c908ed905558a2View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • KAKIMOTO Y, ARMSTRONG MD: The preparation and isolation of D-(-)-beta-aminoisobutyric acid. J Biol Chem. 1961 Dec;236:3283-6. Pubmed: 14453202
  • KAKIMOTO Y, KANAZAWA A, SANO I: IDENTIFICATION OF D(-)-BETA-AMINOISOBUTYRIC ACID IN HUMAN LIVER. Biochim Biophys Acta. 1965 Feb 15;97:376-7. Pubmed: 14292857
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43. Pubmed: 9787093
  • Van Kuilenburg, A. B., Stroomer, A. E., Van Lenthe, H., Abeling, N. G., Van Gennip, A. H. (2004). "New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid?" Biochem J 379:119-124. Pubmed: 14705962
Synthesis Reference:Alauddin, Mian M.; Fissekis, John D.; Conti, Peter S. a-Alkylation of amino acid derivatives: synthesis and chiral resolution of [11C]b-aminoisobutyric acid. Nuclear Medicine and Biology (1997), 24(8), 771-775.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID33094
HMDB IDHMDB02166
Pubchem Compound ID439434
Kegg IDC03284
ChemSpider ID388543
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoBIB

Enzymes

General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate
Gene Name:
gabT
Uniprot ID:
P22256
Molecular weight:
45774
Reactions
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate.
(S)-3-amino-2-methylpropanoate + 2-oxoglutarate = 2-methyl-3-oxopropanoate + L-glutamate.