Showing metabocard for (S)-b-aminoisobutyric acid (MMDBc0029687)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:37:35 UTC
Update Date2022-08-31 17:12:19 UTC
Metabolite IDMMDBc0029687
Metabolite Identification
Common Name(S)-b-aminoisobutyric acid
DescriptionBeta-Aminoisobutyric acid is a non-protein amino acid originating from the catabolism of thymine and valine. Beta-Aminoisobutyric acid occurs in two isomeric forms. The S-enantiomer of beta-Aminoisobutyric acid is predominantly derived from the catabolism of valine. It has been suggested that an altered homoeostasis of b-alanine underlies some of the abnormalities with a dihydropyrimidine dehydrogenase (DPD). DPD constitutes the first step of the pyrimidine degradation pathway, in which the pyrimidine bases uracil and thymine are catabolized to b-alanine and the R-enantiomer of beta-Aminoisobutyric acid respectively. In normal situation 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. (PMID: 14705962 , 14292857 , 14453202 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2697deb98>


  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 #<Metabolite:0x00007fe2697deb98>

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 #<Metabolite:0x00007fe2697deb98>


  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>
MMDBc0029687

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fe2697deb98>

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 #<Metabolite:0x00007fe2697deb98>

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 #<Metabolite:0x00007fe2697deb98>

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 #<Metabolite:0x00007fe2697deb98>

C[C@@H](CN)C(O)=O
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INCHI for #<Metabolite:0x00007fe2697deb98>

InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
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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
Molecular FormulaC4H9NO2
Average Mass103.1198
Monoisotopic Mass103.063328537
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