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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:31:45 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039160

Secondary Accession Numbers

HMDB39160

Metabolite Identification

Common Name

L-Gizzerosine

Description

L-Gizzerosine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on L-Gizzerosine.

Structure

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

HMDB0039160
     RDKit          3D
L-Gizzerosine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.8089   -2.3353   -0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -1.0155   -0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -0.9566   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.3408   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    0.3298    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    1.6617    0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    1.6499    0.9813 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192    0.7718    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188    0.8672    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.0386    0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6933   -1.3597    0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6975   -1.7801    0.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096   -0.7896   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.2644   -0.4491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -0.0215   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2294   -0.3354    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226    1.3309   -0.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0753   -3.0733   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2858   -2.3046    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.9054   -1.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345   -1.7522   -0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021   -1.2338    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.5774   -1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    1.1894    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534    0.1387    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.4545    0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5009    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    1.8642   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    1.5135    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -0.2846    0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    1.0847   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176    1.8961    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    0.5676    2.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -1.9596    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211   -0.8783   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    1.2088   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0018    1.7208   -1.2177 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
M  END


  Mrv0541 05061310532D          

 17 17  0  0  0  0            999 V2000
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409    0.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -0.3495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    0.1934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039160

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CCCCNCCC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N4O2/c12-10(11(16)17)3-1-2-5-13-6-4-9-7-14-8-15-9/h7-8,10,13H,1-6,12H2,(H,14,15)(H,16,17)

> <INCHI_KEY>
LFNFNJYYTXESHV-UHFFFAOYSA-N

> <FORMULA>
C11H20N4O2

> <MOLECULAR_WEIGHT>
240.3021

> <EXACT_MASS>
240.158625904

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.86856752149889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoic acid

> <ALOGPS_LOGP>
-2.16

> <JCHEM_LOGP>
-3.3475140507536647

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.499942383893668

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6815166338577603

> <JCHEM_PKA_STRONGEST_BASIC>
10.198000675755969

> <JCHEM_POLAR_SURFACE_AREA>
104.02999999999999

> <JCHEM_REFRACTIVITY>
64.89439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-{[2-(3H-imidazol-4-yl)ethyl]amino}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039160
     RDKit          3D
L-Gizzerosine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.8089   -2.3353   -0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -1.0155   -0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -0.9566   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.3408   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    0.3298    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    1.6617    0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    1.6499    0.9813 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192    0.7718    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188    0.8672    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.0386    0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6933   -1.3597    0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6975   -1.7801    0.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096   -0.7896   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.2644   -0.4491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -0.0215   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2294   -0.3354    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226    1.3309   -0.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0753   -3.0733   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2858   -2.3046    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.9054   -1.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345   -1.7522   -0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021   -1.2338    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.5774   -1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    1.1894    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534    0.1387    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.4545    0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5009    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    1.8642   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    1.5135    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -0.2846    0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    1.0847   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176    1.8961    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    0.5676    2.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -1.9596    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211   -0.8783   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    1.2088   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0018    1.7208   -1.2177 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.609  -1.171   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.943  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.942  -1.171   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.274  -1.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.800  -1.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.060   0.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.607  -1.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.276  -1.171   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.610  -1.941   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.276   0.369   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.608  -1.941   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -1.830  -0.652   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.446   0.361   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      13.944  -1.171   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.610  -3.481   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1   10                                                       
CONECT    4    6    9                                                       
CONECT    5    2   13                                                       
CONECT    6    4   13                                                       
CONECT    7    9   14                                                       
CONECT    8   14   15                                                       
CONECT    9    4    7   15                                                  
CONECT   10    3   11   12                                                  
CONECT   11   10   16   17                                                  
CONECT   12   10                                                            
CONECT   13    5    6                                                       
CONECT   14    7    8                                                       
CONECT   15    8    9                                                       
CONECT   16   11                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0039160
HETATM    1  N1  UNL     1      -4.809  -2.335  -0.427  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.224  -1.016  -0.657  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.888  -0.957  -0.002  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.179   0.341  -0.166  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.816   0.330   0.515  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.117   1.662   0.330  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.178   1.650   0.981  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.119   0.772   0.355  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.419   0.867   1.125  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.457  -0.039   0.518  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.693  -1.360   0.847  1.00  0.00           C  
HETATM   12  N3  UNL     1       5.698  -1.780   0.067  1.00  0.00           N  
HETATM   13  C10 UNL     1       6.110  -0.790  -0.740  1.00  0.00           C  
HETATM   14  N4  UNL     1       5.339   0.264  -0.449  1.00  0.00           N  
HETATM   15  C11 UNL     1      -5.163  -0.022  -0.145  1.00  0.00           C  
HETATM   16  O1  UNL     1      -6.229  -0.335   0.460  1.00  0.00           O  
HETATM   17  O2  UNL     1      -4.923   1.331  -0.305  1.00  0.00           O  
HETATM   18  H1  UNL     1      -4.075  -3.073  -0.433  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.286  -2.305   0.494  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.084  -0.905  -1.756  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.235  -1.752  -0.420  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.002  -1.234   1.083  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.097   0.577  -1.243  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.727   1.189   0.315  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.953   0.139   1.583  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.212  -0.454   0.012  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.745   2.501   0.688  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.013   1.864  -0.773  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.078   1.513   1.993  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.788  -0.285   0.328  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.271   1.085  -0.688  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.818   1.896   1.002  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.263   0.568   2.160  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.179  -1.960   1.588  1.00  0.00           H  
HETATM   35  H18 UNL     1       6.921  -0.878  -1.475  1.00  0.00           H  
HETATM   36  H19 UNL     1       5.420   1.209  -0.922  1.00  0.00           H  
HETATM   37  H20 UNL     1      -5.002   1.721  -1.218  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   15   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   11   14
CONECT   11   12   34
CONECT   12   13   13
CONECT   13   14   35
CONECT   14   36
CONECT   15   16   16   17
CONECT   17   37
END

HMDB0039160
     RDKit          3D
L-Gizzerosine
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.8089   -2.3353   -0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -1.0155   -0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -0.9566   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.3408   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    0.3298    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    1.6617    0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    1.6499    0.9813 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192    0.7718    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188    0.8672    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.0386    0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6933   -1.3597    0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6975   -1.7801    0.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096   -0.7896   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.2644   -0.4491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -0.0215   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2294   -0.3354    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226    1.3309   -0.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0753   -3.0733   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2858   -2.3046    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.9054   -1.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345   -1.7522   -0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021   -1.2338    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.5774   -1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    1.1894    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534    0.1387    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.4545    0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5009    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    1.8642   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    1.5135    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -0.2846    0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709    1.0847   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176    1.8961    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    0.5676    2.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -1.9596    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211   -0.8783   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    1.2088   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0018    1.7208   -1.2177 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-amino-9-(4-Imidazolyl)-7-azanonanoic acid	HMDB
Gizzerosine	HMDB
N6-(2-(1H-Imidazol-4-yl)ethyl)-L-lysine	HMDB
2-Amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoate	Generator

Chemical Formula

C₁₁H₂₀N₄O₂

Average Molecular Weight

240.3021

Monoisotopic Molecular Weight

240.158625904

IUPAC Name

2-amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoic acid

Traditional Name

2-amino-6-{[2-(3H-imidazol-4-yl)ethyl]amino}hexanoic acid

CAS Registry Number

89238-78-8

SMILES

NC(CCCCNCCC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H20N4O2/c12-10(11(16)17)3-1-2-5-13-6-4-9-7-14-8-15-9/h7-8,10,13H,1-6,12H2,(H,14,15)(H,16,17)

InChI Key

LFNFNJYYTXESHV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Imidazolyl carboxylic acid derivative
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Aralkylamine
Fatty acyl
Fatty acid
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Secondary aliphatic amine
Azacycle
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039160)
Cytoplasm (HMDB: HMDB0039160)

Source

Exogenous

Exogenous (HMDB: HMDB0039160)

Food

Food (HMDB: HMDB0039160)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039160)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	251 - 252 °C	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
Water Solubility	2.08 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	104.03 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.89 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	156.291	31661259
DarkChem	[M-H]-	152.52	31661259
DeepCCS	[M+H]+	151.631	30932474
DeepCCS	[M-H]-	147.717	30932474
DeepCCS	[M-2H]-	185.521	30932474
DeepCCS	[M+Na]+	161.185	30932474
AllCCS	[M+H]+	153.8	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	156.9	32859911
AllCCS	[M+Na]+	157.8	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	159.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	1.67 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8912 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	482.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	352.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	239.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	48.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	319.1 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	245.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1137.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	553.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	44.0 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	536.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1101.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	820.9 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	419.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Gizzerosine	NC(CCCCNCCC1=CN=CN1)C(O)=O	3235.6	Standard polar	33892256
L-Gizzerosine	NC(CCCCNCCC1=CN=CN1)C(O)=O	2399.6	Standard non polar	33892256
L-Gizzerosine	NC(CCCCNCCC1=CN=CN1)C(O)=O	2546.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Gizzerosine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=C[NH]1	2420.8	Semi standard non polar	33892256
L-Gizzerosine,1TMS,isomer #2	C[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O	2591.2	Semi standard non polar	33892256
L-Gizzerosine,1TMS,isomer #3	C[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=C[NH]1	2582.8	Semi standard non polar	33892256
L-Gizzerosine,1TMS,isomer #4	C[Si](C)(C)N1C=NC=C1CCNCCCCC(N)C(=O)O	2524.7	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #1	C[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O[Si](C)(C)C	2530.9	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #1	C[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O[Si](C)(C)C	2407.7	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C	2505.4	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C	2414.5	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=CN1[Si](C)(C)C	2492.0	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=CN1[Si](C)(C)C	2398.8	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #4	C[Si](C)(C)N(C(CCCCNCCC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C	2692.4	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #4	C[Si](C)(C)N(C(CCCCNCCC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C	2516.5	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #5	C[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)C(=O)O	2622.7	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #5	C[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)C(=O)O	2489.1	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #6	C[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O	2604.3	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #6	C[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O	2411.7	Standard non polar	33892256
L-Gizzerosine,2TMS,isomer #7	C[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=CN1[Si](C)(C)C	2622.3	Semi standard non polar	33892256
L-Gizzerosine,2TMS,isomer #7	C[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=CN1[Si](C)(C)C	2470.0	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=C[NH]1)N([Si](C)(C)C)[Si](C)(C)C	2656.9	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=C[NH]1)N([Si](C)(C)C)[Si](C)(C)C	2541.9	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #2	C[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2580.4	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #2	C[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2499.9	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #3	C[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2572.8	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #3	C[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2469.8	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	2578.5	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	2521.8	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #5	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CCC1=CN=C[NH]1	2753.5	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #5	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CCC1=CN=C[NH]1	2622.9	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #6	C[Si](C)(C)N(C(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2748.8	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #6	C[Si](C)(C)N(C(CCCCNCCC1=CN=CN1[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2562.8	Standard non polar	33892256
L-Gizzerosine,3TMS,isomer #7	C[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)C(=O)O	2661.5	Semi standard non polar	33892256
L-Gizzerosine,3TMS,isomer #7	C[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)C(=O)O	2554.1	Standard non polar	33892256
L-Gizzerosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2755.0	Semi standard non polar	33892256
L-Gizzerosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2616.5	Standard non polar	33892256
L-Gizzerosine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=CN1[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2745.2	Semi standard non polar	33892256
L-Gizzerosine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=CN1[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2610.7	Standard non polar	33892256
L-Gizzerosine,4TMS,isomer #3	C[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2630.1	Semi standard non polar	33892256
L-Gizzerosine,4TMS,isomer #3	C[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2570.7	Standard non polar	33892256
L-Gizzerosine,4TMS,isomer #4	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CCC1=CN=CN1[Si](C)(C)C	2811.7	Semi standard non polar	33892256
L-Gizzerosine,4TMS,isomer #4	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CCC1=CN=CN1[Si](C)(C)C	2686.2	Standard non polar	33892256
L-Gizzerosine,5TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2848.8	Semi standard non polar	33892256
L-Gizzerosine,5TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2699.3	Standard non polar	33892256
L-Gizzerosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=C[NH]1	2641.3	Semi standard non polar	33892256
L-Gizzerosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O	2785.5	Semi standard non polar	33892256
L-Gizzerosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=C[NH]1	2760.2	Semi standard non polar	33892256
L-Gizzerosine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC=C1CCNCCCCC(N)C(=O)O	2794.7	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	2927.7	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=C[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	2846.8	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	2943.8	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	2850.5	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C	2971.1	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C	2838.2	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CCCCNCCC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	3065.0	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CCCCNCCC1=CN=C[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	2921.9	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)C(=O)O	3046.7	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)C(=O)O	2916.3	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O	3064.7	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O	2856.1	Standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=CN1[Si](C)(C)C(C)(C)C	3098.3	Semi standard non polar	33892256
L-Gizzerosine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CCCCC(N)C(=O)O)CCC1=CN=CN1[Si](C)(C)C(C)(C)C	2888.7	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=C[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3256.0	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=C[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3126.2	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3213.7	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3092.7	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3217.4	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3091.4	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3272.6	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3121.3	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC1=CN=C[NH]1	3322.2	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC1=CN=C[NH]1	3176.8	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3391.7	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3151.8	Standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3358.0	Semi standard non polar	33892256
L-Gizzerosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3151.0	Standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3569.6	Semi standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3314.8	Standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3584.0	Semi standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNCCC1=CN=CN1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3346.3	Standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3495.8	Semi standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3312.9	Standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC1=CN=CN1[Si](C)(C)C(C)(C)C	3660.4	Semi standard non polar	33892256
L-Gizzerosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCC1=CN=CN1[Si](C)(C)C(C)(C)C	3377.1	Standard non polar	33892256
L-Gizzerosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3882.3	Semi standard non polar	33892256
L-Gizzerosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(CCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3532.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gizzerosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-008d-9500000000-006ba1f557b7a3656e2a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gizzerosine GC-MS (1 TMS) - 70eV, Positive	splash10-0002-4900000000-a37fb3537f0b9595a115	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gizzerosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gizzerosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 10V, Positive-QTOF	splash10-006w-2980000000-16c895e55be26c5cb917	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 20V, Positive-QTOF	splash10-0002-8910000000-8a4cdcda3c906353ed23	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 40V, Positive-QTOF	splash10-000t-9100000000-f2e4e0bd3c9b26b0ac21	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 10V, Negative-QTOF	splash10-000i-0290000000-a6cfe2c0b6ce8b6ad9dc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 20V, Negative-QTOF	splash10-00ds-4980000000-7a0670266de9906a0a5f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 40V, Negative-QTOF	splash10-0fft-9300000000-9f6e0f1cb9f001421484	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 10V, Negative-QTOF	splash10-000i-0090000000-2953c2a18f55f838dfe4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 20V, Negative-QTOF	splash10-000i-1890000000-cd12d6e99f9485c8d3ad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 40V, Negative-QTOF	splash10-0006-9300000000-f530830df96b48e3d647	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 10V, Positive-QTOF	splash10-0006-0190000000-151b3ffe1e5ce4ce7056	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 20V, Positive-QTOF	splash10-001j-9220000000-dd127995904f4d3ddcee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gizzerosine 40V, Positive-QTOF	splash10-000t-9100000000-916452e3944be8bd5147	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018684

KNApSAcK ID

Not Available

Chemspider ID

8552449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10377006

PDB ID

Not Available

ChEBI ID

169532

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-Gizzerosine (HMDB0039160)

MOL for HMDB0039160 (L-Gizzerosine)

3D MOL for HMDB0039160 (L-Gizzerosine)

3D SDF for HMDB0039160 (L-Gizzerosine)

3D-SDF for HMDB0039160 (L-Gizzerosine)

PDB for HMDB0039160 (L-Gizzerosine)

3D PDB for HMDB0039160 (L-Gizzerosine)

SMILES for HMDB0039160 (L-Gizzerosine)

INCHI for HMDB0039160 (L-Gizzerosine)

Structure for HMDB0039160 (L-Gizzerosine)

3D Structure for HMDB0039160 (L-Gizzerosine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra