Showing metabocard for 3-Aminoisobutanoic acid (BMDB0003911)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:35 UTC
Update Date2020-05-21 16:29:02 UTC
BMDB IDBMDB0003911
Secondary Accession Numbers
  • BMDB03911
Metabolite Identification
Common Name3-Aminoisobutanoic acid
Description3-Aminoisobutyrate, also known as 2-methyl-b-alanine or baib, 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. 3-Aminoisobutyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Aminoisobutyrate exists in all eukaryotes, ranging from yeast to humans. 3-Aminoisobutyrate is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Aminomethyl)propionic acidChEBI
2-Methyl-beta-alanineChEBI
3-Amino-2-methylpropanoateChEBI
3-AminoisobutanoateChEBI
alpha-Methyl-beta-alanineChEBI
BAIBChEBI
beta-Aminoisobutyric acidChEBI
DL-beta-Aminoisobutyric acidChEBI
2-(Aminomethyl)propionateGenerator
2-Methyl-b-alanineGenerator
2-Methyl-β-alanineGenerator
3-Amino-2-methylpropanoic acidGenerator
a-Methyl-b-alanineGenerator
Α-methyl-β-alanineGenerator
b-AminoisobutyrateGenerator
b-Aminoisobutyric acidGenerator
beta-AminoisobutyrateGenerator
Β-aminoisobutyrateGenerator
Β-aminoisobutyric acidGenerator
DL-b-AminoisobutyrateGenerator
DL-b-Aminoisobutyric acidGenerator
DL-beta-AminoisobutyrateGenerator
DL-Β-aminoisobutyrateGenerator
DL-Β-aminoisobutyric acidGenerator
3-Aminoisobutyric acidHMDB
(+/-)-3-amino-2-methylpropanoateHMDB
(+/-)-3-amino-2-methylpropanoic acidHMDB
(+/-)-3-aminoisobutyric acidHMDB
(+/-)-b-aminoisobutyric acidHMDB
(+/-)-beta-aminoisobutyric acidHMDB
3-Amino-isobutanoateHMDB
3-Amino-isobutanoic acidHMDB
DL-2-Methyl-b-alanineHMDB
DL-2-Methyl-beta-alanineHMDB
DL-3-Amino-2-methylpropionic acidHMDB
DL-3-Aminoisobutyric acidHMDB
3-Aminoisobutyric acid, (+-)-isomerHMDB
DL-3-Aminoisobutyric acid monohydrateHMDB
3-Aminoisobutyric acid, (S)-isomerHMDB
3-Aminoisobutyric acid, tritium-labeledHMDB
3-Aminoisobutyric acid, (R)-isomerHMDB
3-AminoisobutyrateHMDB
3-Aminoisobutanoic acidChEBI
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name3-amino-2-methylpropanoic acid
Traditional Name(+)-β-aminoisobutyric acid
CAS Registry Number144-90-1
SMILES
CC(CN)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyQCHPKSFMDHPSNR-UHFFFAOYSA-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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
Polarizability10.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003911
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023248
KNApSAcK IDNot Available
Chemspider ID58481
KEGG Compound IDC05145
BioCyc ID3-AMINO-ISOBUTYRATE
BiGG ID41519
Wikipedia Link3-Aminoisobutyric_acid
METLIN ID5472
PubChem Compound64956
PDB IDNot Available
ChEBI ID27389
References
Synthesis ReferenceBalenovic, K.; Jambresic, I.; Ranogajec, I. Preparation of b-aminoisobutyric acid from glycine via the Wolff rearrangement of diazoethyl ketones. Croatica Chemica Acta (1957), 29 87-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Enzymes

Enzyme Details
1. Deaminated glutathione amidase
General function:
Not Available
Specific function:
Catalyzes the hydrolysis of the amide bond in N-(4-oxoglutarate)-L-cysteinylglycine (deaminated glutathione), a metabolite repair reaction to dispose of the harmful deaminated glutathione. Plays a role in cell growth and apoptosis. Has tumor suppressor properties that enhances the apoptotic responsiveness in cancer cells. It is also a negative regulator of primary T-cells.
Gene Name:
NIT1
Uniprot ID:
Q32LH4
Molecular weight:
36240.0
Reactions
Ureidoisobutyric acid + Water → 3-Aminoisobutanoic acid + Carbon dioxide + Ammoniadetails