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Showing metabocard for (S)-beta-Aminoisobutyric acid (HMDB0002166)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2023-02-21 17:16:13 UTC
HMDB IDHMDB0002166
Secondary Accession Numbers
  • HMDB02166
Metabolite Identification
Common Name(S)-beta-Aminoisobutyric acid
Descriptionbeta-Aminoisobutyric acid is a non-protein amino acid originating from the catabolism of thymine and valine. The concentration of beta-aminoisobutyric acid is normally low in urine as beta-aminoisobutyric acid is further catabolized by beta-aminoisobutyrate aminotransferases to methylmalonic acid semialdehyde and propionyl-CoA. beta-Aminoisobutyric acid occurs in two isomeric forms and both enantiomers of beta-aminoisobutyric acid can be detected in human urine and plasma. In plasma, the S-enantiomer is the predominant type due to active renal reabsorption. In contrast, urine almost exclusively contains the R-enantiomer of beta-aminoisobutyric acid, which is eliminated both by filtration and tubular secretion. Persistently increased levels of beta-aminoisobutyric acid have been observed in individuals with a deficiency of R (-)-beta-aminoisobutyrate-pyruvate aminotransferase. 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. The S-enantiomer of beta-aminoisobutyric acid is predominantly derived from the catabolism of valine. 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. In normal individuals with an intact pyrimidine degradation pathway, R-methylmalonic acid semialdehyde can be synthesized directly from the catabolism of thymine. 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 ).
Structure
Data?1676999773
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002166 ((S)-beta-Aminoisobutyric acid)


  Mrv1652306302021032D          

  7  6  0  0  0  0            999 V2000
10000.314510000.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0302 9999.9940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6008 9999.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.313010001.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.743910000.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4591 9999.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.0317 9999.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  2  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  6  0  0  0
  1  3  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

HMDB0002166
     RDKit          3D
(S)-beta-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.4256   -1.3008   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -0.2674    0.4027 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1005    0.0754    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310    0.5839   -0.4231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.9408   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4788    2.0385   -0.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4198    0.8524   -0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838   -1.8549   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -0.7777   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -2.0360   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -0.6973    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471    0.8747    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6338   -0.8043    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    1.5864   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5316   -0.0127   -0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296    0.7989    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  1
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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3D SDF for HMDB0002166 ((S)-beta-Aminoisobutyric acid)


  Mrv1652306302021032D          

  7  6  0  0  0  0            999 V2000
10000.314510000.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0302 9999.9940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6008 9999.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.313010001.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.743910000.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4591 9999.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.0317 9999.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  2  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  6  0  0  0
  1  3  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002166

> <DATABASE_NAME>
hmdb

> <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_KEY>
QCHPKSFMDHPSNR-VKHMYHEASA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.421304909285794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-amino-2-methylpropanoic acid

> <ALOGPS_LOGP>
-2.97

> <JCHEM_LOGP>
-2.6306785728873137

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.17495406481514

> <JCHEM_PKA_STRONGEST_BASIC>
10.324199994995906

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
25.2773

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-β-aminoisobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

HMDB0002166
     RDKit          3D
(S)-beta-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.4256   -1.3008   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -0.2674    0.4027 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1005    0.0754    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310    0.5839   -0.4231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.9408   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4788    2.0385   -0.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4198    0.8524   -0.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838   -1.8549   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -0.7777   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -2.0360   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -0.6973    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471    0.8747    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6338   -0.8043    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    1.5864   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5316   -0.0127   -0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296    0.7989    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  1
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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PDB for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

HEADER    PROTEIN                                 30-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-20         0                                  
HETATM    1  C   UNK     0    8667.2548667.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.5908666.655   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.9218666.651   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.2518668.964   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8669.9228667.428   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8671.2578666.660   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8668.5938665.115   0.000  0.00  0.00           C+0
CONECT    1    4    2    3                                                  
CONECT    2    1    5    7                                                  
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    6                                                       
CONECT    6    5                                                            
CONECT    7    2                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

COMPND    HMDB0002166
HETATM    1  C1  UNL     1      -0.426  -1.301  -0.681  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.337  -0.267   0.403  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.100   0.075   0.760  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.731   0.584  -0.423  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.072   0.941  -0.028  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.479   2.039  -0.132  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.420   0.852  -0.315  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.384  -1.855  -0.605  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.402  -0.778  -1.657  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.395  -2.036  -0.645  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.795  -0.697   1.322  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.047   0.875   1.538  1.00  0.00           H  
HETATM   13  H6  UNL     1       1.634  -0.804   1.117  1.00  0.00           H  
HETATM   14  H7  UNL     1       2.006   1.586  -0.333  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.532  -0.013  -0.728  1.00  0.00           H  
HETATM   16  H9  UNL     1      -3.130   0.799   0.405  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    5   11
CONECT    3    4   12   13
CONECT    4   14   15
CONECT    5    6    6    7
CONECT    7   16
END
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SMILES for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

C[C@@H](CN)C(O)=O
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INCHI for HMDB0002166 ((S)-beta-Aminoisobutyric acid)

InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
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 Weight103.1198
Monoisotopic Molecular Weight103.063328537
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 - 177 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.51531661259
DarkChem[M-H]-116.42931661259
DeepCCS[M+H]+120.30930932474
DeepCCS[M-H]-117.4130932474
DeepCCS[M-2H]-153.94230932474
DeepCCS[M+Na]+128.80630932474
AllCCS[M+H]+126.732859911
AllCCS[M+H-H2O]+122.532859911
AllCCS[M+NH4]+130.732859911
AllCCS[M+Na]+131.932859911
AllCCS[M-H]-124.732859911
AllCCS[M+Na-2H]-128.732859911
AllCCS[M+HCOO]-133.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.28 minutes32390414
Predicted by Siyang on May 30, 20228.5725 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20226.16 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid350.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid484.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid326.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid51.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid211.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid67.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid275.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid229.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)743.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid557.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid35.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid620.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid199.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid269.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate636.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA471.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water339.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-beta-Aminoisobutyric acidC[C@@H](CN)C(O)=O1840.6Standard polar33892256
(S)-beta-Aminoisobutyric acidC[C@@H](CN)C(O)=O1015.3Standard non polar33892256
(S)-beta-Aminoisobutyric acidC[C@@H](CN)C(O)=O1032.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-beta-Aminoisobutyric acid,1TMS,isomer #1C[C@@H](CN)C(=O)O[Si](C)(C)C1051.8Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,1TMS,isomer #2C[C@@H](CN[Si](C)(C)C)C(=O)O1206.4Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #1C[C@@H](CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1230.4Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #1C[C@@H](CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1249.7Standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #1C[C@@H](CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1331.9Standard polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #2C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1412.2Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #2C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1357.2Standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TMS,isomer #2C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1608.9Standard polar33892256
(S)-beta-Aminoisobutyric acid,3TMS,isomer #1C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1464.4Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,3TMS,isomer #1C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1414.9Standard non polar33892256
(S)-beta-Aminoisobutyric acid,3TMS,isomer #1C[C@@H](CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1339.4Standard polar33892256
(S)-beta-Aminoisobutyric acid,1TBDMS,isomer #1C[C@@H](CN)C(=O)O[Si](C)(C)C(C)(C)C1282.3Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,1TBDMS,isomer #2C[C@@H](CN[Si](C)(C)C(C)(C)C)C(=O)O1450.9Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #1C[C@@H](CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1668.6Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #1C[C@@H](CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1679.3Standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #1C[C@@H](CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1627.1Standard polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #2C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O1828.1Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #2C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O1761.4Standard non polar33892256
(S)-beta-Aminoisobutyric acid,2TBDMS,isomer #2C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O1785.6Standard polar33892256
(S)-beta-Aminoisobutyric acid,3TBDMS,isomer #1C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2095.5Semi standard non polar33892256
(S)-beta-Aminoisobutyric acid,3TBDMS,isomer #1C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2054.2Standard non polar33892256
(S)-beta-Aminoisobutyric acid,3TBDMS,isomer #1C[C@@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1764.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-beta-Aminoisobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-59e52601f90d8e636d612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-beta-Aminoisobutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00ar-9200000000-0eb92539979a9fa36dbd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-beta-Aminoisobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, negative-QTOFsplash10-0udi-1900000000-aaccebe5d4a868bc32bf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 2V, negative-QTOFsplash10-0udi-2900000000-4f4e49fe169d5c21efc12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 2V, negative-QTOFsplash10-0udi-4900000000-f32e82420f5efb60456e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 3V, negative-QTOFsplash10-0uk9-6900000000-cb0ef82b397e243721422020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 3V, negative-QTOFsplash10-0uk9-8900000000-31fc31847c8771693d152020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 3V, negative-QTOFsplash10-0fk9-9600000000-6379643466e30660a05b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 4V, negative-QTOFsplash10-00di-9300000000-97e8a7125780e41fceaf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 5V, negative-QTOFsplash10-05fr-9200000000-8f0488fe62603d1215362020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 5V, negative-QTOFsplash10-0ab9-9100000000-84e07fbee3e3325022652020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 6V, negative-QTOFsplash10-0a4i-9000000000-3634b730902e2e080b562020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid n/a 7V, negative-QTOFsplash10-00di-9000000000-1b9078e3902a11473fa02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 0V, positive-QTOFsplash10-0udi-1900000000-76d19f44560e6b1b6f802020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 0V, positive-QTOFsplash10-0udi-1900000000-bd4e85f35b448a2b75402020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 0V, positive-QTOFsplash10-0udi-2900000000-b1371ec53be10ec9c4112020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, positive-QTOFsplash10-0udi-3900000000-d16b3475fcdfed5038d52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, positive-QTOFsplash10-0udi-4900000000-cd34930bbcb805c7525f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, positive-QTOFsplash10-0udr-5900000000-4b73ac1046680185a9812020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, positive-QTOFsplash10-0udr-6900000000-a911da27982a560a6cf12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid Orbitrap 1V, positive-QTOFsplash10-0udr-8900000000-91a255aae27e4e4aabb82020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 10V, Positive-QTOFsplash10-0f79-9300000000-30669ed04aadf3d3f0402015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 20V, Positive-QTOFsplash10-000l-9000000000-ca65637476e64152c44e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-04d1648391d3f90db2262015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 10V, Negative-QTOFsplash10-0udi-3900000000-ec54fcce079024a623442015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 20V, Negative-QTOFsplash10-0zfr-9500000000-0394f399cdf5df93c5df2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-beta-Aminoisobutyric acid 40V, Negative-QTOFsplash10-0a4l-9000000000-d0c495c908ed905558a22015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.03 +/- 0.34 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified7.0 +/- 6.6 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified10.0 +/- 9.0 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified4.3 +/- 2.9 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified11.31 +/- 16.96 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified14.70 +/- 38.44 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified2.04-354.79 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified<110.86 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.70-117.53 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.71-57.80 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.24-32.35 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<34.048 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH ID3AIB
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAlauddin, Mian M.; Fissekis, John D.; Conti, Peter S. a-Alkylation of amino acid derivatives: synthesis and chiral resolution of [11C]b-aminoisobutyric acid. Nuclear Medicine and Biology (1997), 24(8), 771-775.
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:14705962 ]
  2. Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43. [PubMed:9787093 ]
  3. KAKIMOTO Y, KANAZAWA A, SANO I: IDENTIFICATION OF D(-)-BETA-AMINOISOBUTYRIC ACID IN HUMAN LIVER. Biochim Biophys Acta. 1965 Feb 15;97:376-7. [PubMed:14292857 ]
  4. 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
Reactions
(S)-beta-Aminoisobutyric acid + Oxoglutaric acid → 2-Methyl-3-oxopropanoic acid + Glutamic aciddetails
(S)-beta-Aminoisobutyric acid + Oxoglutaric acid → (S)-Methylmalonic acid semialdehyde + Glutamic aciddetails