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Record Information
Version3.6
Creation Date2006-05-22 14:17:47 UTC
Update Date2016-02-11 01:05:33 UTC
HMDB IDHMDB02299
Secondary Accession NumbersNone
Metabolite Identification
Common Name(R)-b-aminoisobutyric acid
Description(R)-b-aminoisobutyric acid is the product of the catabolism of the pyrimidine bases uracil and thymine by the enzyme dihydropyrimidine dehydrogenase (DPD), in what constitutes the first step of the pyrimidine degradation pathway. The other products of the reaction is beta-alanine (PMID 14705962 ).
Structure
Thumb
Synonyms
ValueSource
(2R)-3-amino-2-Methylpropanoic acidChEBI
(R)-3-amino-2-MethylpropanoateChEBI
(R)-beta-Aminoisobutyric acidChEBI
D-3-amino-IsobutanoateChEBI
(2R)-3-amino-2-MethylpropanoateGenerator
(R)-3-AminoisobutyrateGenerator
(R)-3-amino-2-Methylpropanoic acidGenerator
(R)-b-AminoisobutyrateGenerator
(R)-b-Aminoisobutyric acidGenerator
(R)-beta-AminoisobutyrateGenerator
(R)-β-aminoisobutyrateGenerator
(R)-β-aminoisobutyric acidGenerator
D-3-amino-Isobutanoic acidGenerator
(-)-b-AminoisobutyrateHMDB
(-)-b-Aminoisobutyric acidHMDB
(-)-beta-AminoisobutyrateHMDB
(-)-beta-Aminoisobutyric acidHMDB
(2R)-3-amino-2-Methyl-propanoateHMDB
(2R)-3-amino-2-Methyl-propanoic acidHMDB
(R)-3-amino-2-Methyl-propanoateHMDB
(R)-3-amino-2-Methyl-propanoic acidHMDB
D-2-Methyl-b-alanineHMDB
D-3-amino-2-MethylpropanoateHMDB
D-3-amino-2-Methylpropanoic acidHMDB
D-3-amino-2-MethylpropionateHMDB
D-3-amino-2-Methylpropionic acidHMDB
D-b-AminoisobutyrateHMDB
D-b-Aminoisobutyric acidHMDB
delta-2-Methyl-beta-alanineHMDB
delta-3-amino-2-MethylpropanoateHMDB
delta-3-amino-2-Methylpropanoic acidHMDB
delta-3-amino-2-MethylpropionateHMDB
delta-3-amino-2-Methylpropionic acidHMDB
delta-beta-AminoisobutyrateHMDB
delta-beta-Aminoisobutyric acidHMDB
R-b-AminoisobutyrateHMDB
R-beta-AminoisobutyrateHMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name(2R)-3-amino-2-methylpropanoic acid
Traditional Name(R)-β-aminoisobutyric acid
CAS Registry Number2140-95-6
SMILES
C[C@H](CN)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1
InChI KeyInChIKey=QCHPKSFMDHPSNR-GSVOUGTGSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility367.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.28 m3·mol-1ChemAxon
Polarizability10.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022955
KNApSAcK IDNot Available
Chemspider ID4573585
KEGG Compound IDC01205
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02299
Metagene LinkHMDB02299
METLIN ID6599
PubChem Compound5459822
PDB IDNot Available
ChEBI ID16320
References
Synthesis ReferencePollock, Glenn. Preparation of R(-)-b-aminoisobutyric acid using Saccharomyces cerevisiae. Unexpected result. Analytical Biochemistry (1974), 57(1), 82-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [10686279 ]
  2. Van 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. [14705962 ]

Enzymes

General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
Reactions
(R)-b-aminoisobutyric acid + Pyruvic acid → 2-Methyl-3-oxopropanoic acid + L-Alaninedetails