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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-08-27 21:47:38 UTC

Update Date

2021-09-14 15:44:49 UTC

HMDB ID

HMDB0242176

Secondary Accession Numbers

None

Metabolite Identification

Common Name

gamma-Glutamyl-2-aminobutyrate

Description

gamma-Glutamyl-2-aminobutyrate, also known as g-glu-abu(1-), belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on gamma-Glutamyl-2-aminobutyrate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0242176
     RDKit          3D
gamma-Glutamyl-2-aminobutyrate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.1505   -0.9011    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.0318    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196   -0.0363   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697    0.8369   -0.5561 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.3581   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.8609   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764    1.2881   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.7247   -0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -0.0045    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4686   -1.1745    0.7309 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5693   -0.4185    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.5099    0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -1.7319   -0.2642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.2836    0.4187   -1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    1.0518   -1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0746    0.1575   -2.8642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.0223   -0.4680    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859   -1.9036    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -1.0579   -0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.3172    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.0788    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -1.0778   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188    1.8335   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874    1.8749   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    2.1180   -0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.0456   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590    1.5753   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.6721    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -1.9560    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -1.6599    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.0077    1.2487 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
M  CHG  3  10   1  13  -1  16  -1
M  END


  Mrv1652305062021442D          

 16 15  0  0  1  0            999 V2000
    4.5080   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4438    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2063    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.2063    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0  0  0  0
  2 14  1  0  0  0  0
  3 14  2  0  0  0  0
  4 16  1  0  0  0  0
  5 16  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 16  1  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  3   2  -1   4  -1   7   1
M  END
> <DATABASE_ID>
HMDB0242176

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(NC(=O)CCC([NH3+])C([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O5/c1-2-6(9(15)16)11-7(12)4-3-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/p-1

> <INCHI_KEY>
FUZOZPRKGAXGOB-UHFFFAOYSA-M

> <FORMULA>
C9H15N2O5

> <MOLECULAR_WEIGHT>
231.229

> <EXACT_MASS>
231.098645171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.192413800035105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-azaniumyl-4-[(1-carboxypropyl)carbamoyl]butanoate

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-3.2900401176616234

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9030145824641873

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.017225849539196

> <JCHEM_PKA_STRONGEST_BASIC>
9.312077246711887

> <JCHEM_POLAR_SURFACE_AREA>
137.0

> <JCHEM_REFRACTIVITY>
86.07609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ammonio-4-[(1-carboxypropyl)carbamoyl]butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242176
     RDKit          3D
gamma-Glutamyl-2-aminobutyrate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.1505   -0.9011    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.0318    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196   -0.0363   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697    0.8369   -0.5561 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.3581   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.8609   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764    1.2881   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.7247   -0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -0.0045    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4686   -1.1745    0.7309 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5693   -0.4185    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.5099    0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -1.7319   -0.2642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.2836    0.4187   -1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    1.0518   -1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0746    0.1575   -2.8642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.0223   -0.4680    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859   -1.9036    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -1.0579   -0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.3172    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.0788    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -1.0778   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188    1.8335   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874    1.8749   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    2.1180   -0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.0456   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590    1.5753   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.6721    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -1.9560    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -1.6599    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.0077    1.2487 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
M  CHG  3  10   1  13  -1  16  -1
M  END

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  O   UNK     0       8.415  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.750   2.695   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0      11.082   2.695   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -0.385   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0       4.414   1.925   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081   0.385   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.750  -0.385   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      11.082  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   16                                                            
CONECT    5   16                                                            
CONECT    6   11   12                                                       
CONECT    7    9                                                            
CONECT    8    9   10                                                       
CONECT    9    7    8   14                                                  
CONECT   10    8   12                                                       
CONECT   11    6   13   16                                                  
CONECT   12    1    6   10                                                  
CONECT   13   11   15                                                       
CONECT   14    2    3    9                                                  
CONECT   15   13                                                            
CONECT   16    4    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0242176
HETATM    1  C1  UNL     1      -4.150  -0.901   0.872  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.963   0.032   0.874  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.320  -0.036  -0.496  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.170   0.837  -0.556  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.151   0.358  -0.840  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.261  -0.861  -1.035  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.276   1.288  -0.888  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.650   0.725  -0.891  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.135  -0.005   0.291  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.469  -1.175   0.731  1.00  0.00           N1+
HETATM   11  C8  UNL     1       4.569  -0.418   0.008  1.00  0.00           C  
HETATM   12  O2  UNL     1       5.415   0.510   0.039  1.00  0.00           O  
HETATM   13  O3  UNL     1       4.908  -1.732  -0.264  1.00  0.00           O1-
HETATM   14  C9  UNL     1      -3.284   0.419  -1.517  1.00  0.00           C  
HETATM   15  O4  UNL     1      -4.307   1.052  -1.152  1.00  0.00           O  
HETATM   16  O5  UNL     1      -3.075   0.158  -2.864  1.00  0.00           O1-
HETATM   17  H1  UNL     1      -5.022  -0.468   1.403  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.886  -1.904   1.271  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.467  -1.058  -0.175  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.263  -0.317   1.666  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.258   1.079   1.123  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.022  -1.078  -0.695  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.319   1.834  -0.387  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.187   1.875  -1.867  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.161   2.118  -0.131  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.687   0.046  -1.806  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.359   1.575  -1.134  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.228   0.672   1.186  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.411  -1.956   0.028  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.060  -1.660   1.511  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.578  -1.008   1.249  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   14   22
CONECT    4    5   23
CONECT    5    6    6    7
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   11   28
CONECT   10   29   30   31
CONECT   11   12   12   13
CONECT   14   15   15   16
END

HMDB0242176
     RDKit          3D
gamma-Glutamyl-2-aminobutyrate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.1505   -0.9011    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.0318    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196   -0.0363   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697    0.8369   -0.5561 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.3581   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.8609   -1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764    1.2881   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.7247   -0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -0.0045    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4686   -1.1745    0.7309 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5693   -0.4185    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147    0.5099    0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -1.7319   -0.2642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.2836    0.4187   -1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    1.0518   -1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0746    0.1575   -2.8642 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.0223   -0.4680    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859   -1.9036    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -1.0579   -0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.3172    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.0788    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -1.0778   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188    1.8335   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874    1.8749   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    2.1180   -0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.0456   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590    1.5753   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.6721    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -1.9560    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -1.6599    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775   -1.0077    1.2487 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
M  CHG  3  10   1  13  -1  16  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
g-Glutamyl-2-aminobutyrate	Generator
g-Glutamyl-2-aminobutyric acid	Generator
gamma-Glutamyl-2-aminobutyric acid	Generator
Γ-glutamyl-2-aminobutyrate	Generator
Γ-glutamyl-2-aminobutyric acid	Generator
g-Glu-abu(1-)	HMDB
Γ-glu-abu(1-)	HMDB
gamma-Glutamyl-2-aminobutyrate	ChEBI

Chemical Formula

C₉H₁₅N₂O₅

Average Molecular Weight

231.229

Monoisotopic Molecular Weight

231.098645171

IUPAC Name

2-azaniumyl-4-[(1-carboxypropyl)carbamoyl]butanoate

Traditional Name

2-ammonio-4-[(1-carboxypropyl)carbamoyl]butanoate

CAS Registry Number

Not Available

SMILES

CCC(NC(=O)CCC([NH3+])C([O-])=O)C([O-])=O

InChI Identifier

InChI=1S/C9H16N2O5/c1-2-6(9(15)16)11-7(12)4-3-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/p-1

InChI Key

FUZOZPRKGAXGOB-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic nitrogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-3.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.08 m³·mol⁻¹	ChemAxon
Polarizability	22.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	149.135	30932474
DeepCCS	[M-H]-	146.67	30932474
DeepCCS	[M-2H]-	180.387	30932474
DeepCCS	[M+Na]+	156.633	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.0586 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1191.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	245.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	310.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	430.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	681.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	288.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1070.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	551.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	274.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	282.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-2-aminobutyrate	CCC(NC(=O)CCC([NH3+])C([O-])=O)C([O-])=O	2797.8	Standard polar	33892256
gamma-Glutamyl-2-aminobutyrate	CCC(NC(=O)CCC([NH3+])C([O-])=O)C([O-])=O	1689.3	Standard non polar	33892256
gamma-Glutamyl-2-aminobutyrate	CCC(NC(=O)CCC([NH3+])C([O-])=O)C([O-])=O	1676.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-2-aminobutyrate,1TMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C	1808.9	Semi standard non polar	33892256
gamma-Glutamyl-2-aminobutyrate,1TMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C	1833.7	Standard non polar	33892256
gamma-Glutamyl-2-aminobutyrate,1TMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C	2533.1	Standard polar	33892256
gamma-Glutamyl-2-aminobutyrate,1TBDMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C(C)(C)C	2066.0	Semi standard non polar	33892256
gamma-Glutamyl-2-aminobutyrate,1TBDMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C(C)(C)C	2062.9	Standard non polar	33892256
gamma-Glutamyl-2-aminobutyrate,1TBDMS,isomer #1	CCC(C(=O)[O-])N(C(=O)CCC([NH3+])C(=O)[O-])[Si](C)(C)C(C)(C)C	2577.5	Standard polar	33892256

Spectra

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21232230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78437958

PDB ID

Not Available

ChEBI ID

133093

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kong SW, Hernandez-Ferrer C: Assessment of coverage for endogenous metabolites and exogenous chemical compounds using an untargeted metabolomics platform. Pac Symp Biocomput. 2020;25:587-598. [PubMed:31797630 ]

Showing metabocard for gamma-Glutamyl-2-aminobutyrate (HMDB0242176)

MOL for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

3D MOL for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

3D SDF for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

3D-SDF for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

PDB for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

3D PDB for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

SMILES for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

INCHI for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

Structure for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

3D Structure for HMDB0242176 (gamma-Glutamyl-2-aminobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

NMR Spectra