Showing metabocard for L-alpha-Aminobutyric acid (MMDBc0000103)

Show more...
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:35:59 UTC
Update Date2024-04-30 19:31:04 UTC
Metabolite IDMMDBc0000103
Metabolite Identification
Common NameL-alpha-Aminobutyric acid
DescriptionL-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, ethylglycine, or L-butyrine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-aminobutyric acid is soluble (in water) and is a moderately acidic compound (based on its pKa). L-alpha-Aminobutyric acid is a non-proteogenic amino acid that can be found in the human kidney, in liver tissues, and in most biofluids or excreta (e.g. feces, breast milk, urine, and blood). Within the cell, L-alpha-aminobutyric acid is primarily located in the cytoplasm. alpha-Aminobutyric acid is biosynthesized by transaminating oxobutyrate, a metabolite in isoleucine biosynthesis. As a non-proteogenic amino acid, alpha-aminobutyric acid can be used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing alpha-aminobutyric acid is ophthalmic acid, which was first isolated from calf lens. alpha-Aminobutyric acid is a non-essential amino acid that is primarily derived from the catabolism of methionine, threonine, and serine. High protein diets can result in significantly higher alpha-aminobutyrate levels in plasma (PMID: 26227325 ). alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency (PMID: 420125 ). alpha-Aminobutyric acid is one of the three isomers of aminobutyric acid. The two other are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd5b7eac1c8>

  Mrv1652305271900182D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  6  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd5b7eac1c8>

HMDB0000452
     RDKit          3D
L-alpha-Aminobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.9230   -0.3615    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    0.2472   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.4670    0.1580 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4127    1.0413   -0.6931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -0.8323    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.5681    1.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -1.2988    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -0.1110    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016   -1.4744    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.0420    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    1.2203   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.3993   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258    1.1454    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.0440   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6212    0.4415   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6032    0.3048 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
  3  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  0
  2 12  1  0
  3 13  1  1
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd5b7eac1c8>

  Mrv1652305271900182D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  6  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000103

> <DATABASE_NAME>
MIME

> <SMILES>
CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

> <INCHI_KEY>
QWCKQJZIFLGMSD-VKHMYHEASA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.3377399468906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-aminobutanoic acid

> <ALOGPS_LOGP>
-2.55

> <JCHEM_LOGP>
-2.3181498124844198

> <ALOGPS_LOGS>
0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.615755119614637

> <JCHEM_PKA_STRONGEST_BASIC>
9.53467345401491

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
25.0213

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-2-aminobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fd5b7eac1c8>

HMDB0000452
     RDKit          3D
L-alpha-Aminobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.9230   -0.3615    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    0.2472   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.4670    0.1580 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4127    1.0413   -0.6931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -0.8323    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.5681    1.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -1.2988    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -0.1110    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016   -1.4744    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.0420    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    1.2203   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.3993   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258    1.1454    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.0440   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6212    0.4415   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6032    0.3048 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
  3  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  0
  2 12  1  0
  3 13  1  1
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

PDB for #<Metabolite:0x00007fd5b7eac1c8>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8664.7238664.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3898665.117   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8662.0558664.348   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.3898666.656   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8666.0588665.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.3908664.348   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8664.7238662.807   0.000  0.00  0.00           N+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
CONECT    7    1                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for #<Metabolite:0x00007fd5b7eac1c8>

COMPND    HMDB0000452
HETATM    1  C1  UNL     1      -1.923  -0.362   0.382  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.896   0.247  -0.540  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.427   0.467   0.158  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.413   1.041  -0.693  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.935  -0.832   0.666  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.265  -1.568   1.449  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.188  -1.299   0.295  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.632  -0.111   1.421  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.902  -1.474   0.203  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.915   0.042   0.094  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.264   1.220  -0.889  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.755  -0.399  -1.433  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.226   1.145   1.012  1.00  0.00           H  
HETATM   14  H7  UNL     1       1.270   2.044  -0.916  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.621   0.442  -1.514  1.00  0.00           H  
HETATM   16  H9  UNL     1       2.942  -0.603   0.305  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    5   13
CONECT    4   14   15
CONECT    5    6    6    7
CONECT    7   16
END
Download

SMILES for #<Metabolite:0x00007fd5b7eac1c8>

CC[C@H](N)C(O)=O
Download

INCHI for #<Metabolite:0x00007fd5b7eac1c8>

InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
Download
Synonyms
Molecular FormulaC4H9NO2
Average Mass103.1198
Monoisotopic Mass103.063328537
IUPAC Name(2S)-2-aminobutanoic acid
Traditional Name(-)-2-aminobutyric acid
CAS Registry Number1492-24-6
SMILES
CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N