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Showing Compound (S)-beta-Aminoisobutyric acid (FDB022878)

Record Information
Version1.0
Creation date2011-09-21 00:20:58 UTC
Update date2020-09-17 15:40:46 UTC
Primary IDFDB022878
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-beta-Aminoisobutyric acid
Description(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.
CAS Number4249-19-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(S)-3-Amino-2-methylpropanoic acidChEBI
(S)-3-Amino-isobutanoic acidChEBI
(S)-3-Amino-isobutyric acidChEBI
L-3-Amino-isobutanoic acidChEBI
L-3-Amino-isobutyric acidChEBI
(S)-3-AminoisobutyrateKegg
L-3-AminoisobutyrateKegg
(S)-3-AminoisobutanoateKegg
(S)-3-Amino-2-methylpropanoateKegg
(S)-beta-AminoisobutyrateKegg
(S)-3-Amino-isobutanoateGenerator
(S)-3-Amino-isobutyrateGenerator
L-3-Amino-isobutanoateGenerator
L-3-Amino-isobutyrateGenerator
(S)-3-Aminoisobutyric acidGenerator
L-3-Aminoisobutyric acidGenerator
(S)-3-Aminoisobutanoic acidGenerator
(S)-b-AminoisobutyrateGenerator
(S)-b-Aminoisobutyric acidGenerator
(S)-Β-aminoisobutyrateGenerator
(S)-Β-aminoisobutyric acidGenerator
(S)-beta-Aminoisobutyric acidChEBI
(+)-a-Methyl-b-alanineHMDB
(+)-alpha-Methyl-beta-alanineHMDB
(+)-b-Aminoisobutyric acidHMDB
(+)-beta-Aminoisobutyric acidHMDB
(S)-3-amino-2-Methyl-propanoateHMDB
(S)-3-amino-2-Methyl-propanoic acidHMDB
L-2-Methyl-b-alanineHMDB
L-2-Methyl-beta-alanineHMDB
L-3-amino-2-MethylpropanoateHMDB
L-3-amino-2-Methylpropanoic acidHMDB
L-3-amino-2-Methylpropionic acidHMDB
L-b-AminoisobutyrateHMDB
L-b-Aminoisobutyric acidHMDB
L-beta-AminoisobutyrateHMDB
L-beta-Aminoisobutyric acidHMDB
S-b-AminoisobutyrateHMDB
S-beta-AminoisobutyrateHMDB
S-beta-Aminoisobutyric acidHMDB
(S)-3-amino-2-methyl-Propanoatehmdb
(S)-3-amino-2-methyl-Propanoic acidhmdb
(S)-β-aminoisobutyrateGenerator
(S)-β-aminoisobutyric acidGenerator
L-2-methyl-b-Alaninehmdb
L-2-methyl-beta-Alaninehmdb
L-3-Amino-2-methylpropanoatehmdb
L-3-Amino-2-methylpropanoic acidhmdb
L-3-Amino-2-methylpropionic acidhmdb
L-b-aminoisobutyratehmdb
L-beta-aminoisobutyratehmdb
S-b-aminoisobutyratehmdb
S-beta-aminoisobutyratehmdb
S-beta-aminoisobutyric acidhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H9NO2
IUPAC name(2S)-3-amino-2-methylpropanoic acid
InChI IdentifierInChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQCHPKSFMDHPSNR-VKHMYHEASA-N
Isomeric SMILESC[C@@H](CN)C(O)=O
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-beta-Aminoisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-59e52601f90d8e636d61Spectrum
Predicted GC-MS(S)-beta-Aminoisobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ar-9200000000-0eb92539979a9fa36dbdSpectrum
Predicted GC-MS(S)-beta-Aminoisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-1900000000-aaccebe5d4a868bc32bf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-2900000000-4f4e49fe169d5c21efc12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-4900000000-f32e82420f5efb60456e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0uk9-6900000000-cb0ef82b397e243721422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0uk9-8900000000-31fc31847c8771693d152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0fk9-9600000000-6379643466e30660a05b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-9300000000-97e8a7125780e41fceaf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-05fr-9200000000-8f0488fe62603d1215362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0ab9-9100000000-84e07fbee3e3325022652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-3634b730902e2e080b562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-00di-9000000000-1b9078e3902a11473fa02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-1900000000-76d19f44560e6b1b6f802020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-1900000000-bd4e85f35b448a2b75402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-2900000000-b1371ec53be10ec9c4112020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-3900000000-d16b3475fcdfed5038d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-4900000000-cd34930bbcb805c7525f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-5900000000-4b73ac1046680185a9812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-6900000000-a911da27982a560a6cf12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udr-8900000000-91a255aae27e4e4aabb82020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9300000000-30669ed04aadf3d3f0402015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-ca65637476e64152c44e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-04d1648391d3f90db2262015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-ec54fcce079024a623442015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9500000000-0394f399cdf5df93c5df2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-d0c495c908ed905558a22015-09-15View Spectrum
NMRNot Available
ChemSpider ID388543
ChEMBL IDNot Available
KEGG Compound IDC03284
Pubchem Compound ID439434
Pubchem Substance IDNot Available
ChEBI ID33094
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02166
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference