Showing Compound Card for (S)-beta-Aminoisobutyric acid (CDB005159)

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Record Information
Version1.0
Created at2020-04-17 19:15:16 UTC
Updated at2020-11-18 16:39:27 UTC
CannabisDB IDCDB005159
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. In addition, transient high levels of beta-aminoisobutyric acid have been observed under a variety of pathological conditions such as lead poisoning, starvation, in total body irradiation, and in a number of malignancies. It has been suggested that altered homeostasis of beta-alanine underlies some of the clinical abnormalities encountered in patients with a dihydropyrimidine dehydrogenase (DPD) deficiency. DPD constitutes the first step of the pyrimidine degradation pathway, in which the pyrimidine bases uracil and thymine are catabolized to beta-alanine and the R-enantiomer of beta-aminoisobutyric acid respectively. 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 in plasma (PMID: 14705962 , 14292857 , 14453202 ). The S-enantiomer of beta-aminoisobutyric acid is predominantly derived from the catabolism of valine. (S)-beta-Aminoisobutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC4H9NO2
Average Molecular Weight103.12
Monoisotopic Molecular Weight103.0633
IUPAC Name(2S)-3-amino-2-methylpropanoic acid
Traditional NameL-β-aminoisobutyric acid
CAS Registry Number4249-19-8
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-/m0/s1
InChI KeyQCHPKSFMDHPSNR-VKHMYHEASA-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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 - 177 °CNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002166
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022878
KNApSAcK IDNot Available
Chemspider ID388543
KEGG Compound IDC03284
BioCyc IDCPD-466
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6520
PubChem Compound439434
PDB IDNot Available
ChEBI ID33094
References
General References
  1. 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. doi: 10.1042/BJ20031463. [PubMed:14705962 ]
  2. KAKIMOTO Y, KANAZAWA A, SANO I: IDENTIFICATION OF D(-)-BETA-AMINOISOBUTYRIC ACID IN HUMAN LIVER. Biochim Biophys Acta. 1965 Feb 15;97:376-7. doi: 10.1016/0304-4165(65)90114-5. [PubMed:14292857 ]
  3. KAKIMOTO Y, ARMSTRONG MD: The preparation and isolation of D-(-)-beta-aminoisobutyric acid. J Biol Chem. 1961 Dec;236:3283-6. [PubMed:14453202 ]

Enzymes

Enzyme Details
1. 4-aminobutyrate aminotransferase, mitochondrial
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405