Showing metabocard for (R)-b-aminoisobutyric acid (BMDB0002299)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:53:47 UTC
Update Date2020-04-22 15:10:33 UTC
BMDB IDBMDB0002299
Secondary Accession Numbers
  • BMDB02299
Metabolite Identification
Common Name(R)-b-aminoisobutyric acid
Description(R)-beta-Aminoisobutyric acid, also known as (R)-b-aminoisobutyrate or D-3-amino-isobutanoate, 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 (R)-beta-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on (R)-beta-Aminoisobutyric acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R)-3-Amino-2-methylpropanoateChEBI
D-3-Amino-isobutanoateChEBI
(R)-3-AminoisobutyrateKegg
D-3-AminoisobutanoateKegg
(R)-beta-AminoisobutyrateKegg
(R)-3-Amino-2-methylpropanoic acidGenerator
D-3-Amino-isobutanoic acidGenerator
(R)-3-Aminoisobutyric acidGenerator
D-3-Aminoisobutanoic acidGenerator
(R)-b-AminoisobutyrateGenerator
(R)-b-Aminoisobutyric acidGenerator
(R)-Β-aminoisobutyrateGenerator
(R)-Β-aminoisobutyric acidGenerator
(2R)-3-amino-2-Methylpropanoic acidChEBI, HMDB
(R)-beta-Aminoisobutyric acidChEBI
(2R)-3-amino-2-MethylpropanoateGenerator, HMDB
(-)-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
(R)-b-Amino-isobutyrateGenerator, HMDB
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 KeyQCHPKSFMDHPSNR-GSVOUGTGSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability10.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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, Positivesplash10-0fk9-9600000000-cc7feca41328ecce5182View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-73f528c6a325150832f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-4d21706fbeb6fb3bcdf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-56dadc563410f528ed7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-3fb811fcffbd6b2d2e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9800000000-6408ed0365461b1d2f8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-82524943b0495ba8c3cfView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002299
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022955
KNApSAcK IDNot Available
Chemspider ID4573585
KEGG Compound IDC01205
BioCyc IDCPD-471
BiGG IDNot Available
Wikipedia LinkNot Available
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Alanine--glyoxylate aminotransferase 2, mitochondrial
General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
AGXT2
Uniprot ID:
Q17QF0
Molecular weight:
57226.0