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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:37 UTC

Update Date

2021-09-14 15:20:33 UTC

HMDB ID

HMDB0029083

Secondary Accession Numbers

HMDB29083

Metabolite Identification

Common Name

Tryptophyl-Glycine

Description

Tryptophyl-Glycine is a dipeptide composed of tryptophan and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.

Structure

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

HMDB0247340
     RDKit          3D
Tryptophylglycine
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.0126    0.0539    1.4261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.7181    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486   -0.2371   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.4359    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.9773    1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -0.9681    1.8944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188   -0.4357    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9799   -0.1748    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4393    0.3974   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    0.7376   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2238    0.4854   -1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -0.0949   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.6668   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290   -1.2666   -1.6392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    0.0777   -0.0049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563    0.1582   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    0.9844    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221    1.5247    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7982    1.2014   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.3634    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.0389    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -1.8032    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.8411   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332   -0.7694   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634   -1.3576    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342   -1.3201    2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6231   -0.4518    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5165    0.5935   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993    1.1807   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.7375   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    0.5824    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6840   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752   -0.8589   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8623    1.6208   -1.3416 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 12  4  1  0
 12  7  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END


  Mrv1652304062014182D          

 19 20  0  0  0  0            999 V2000
   -0.2461    0.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605    1.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -0.4209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    0.1266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972   -0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1902   -0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -1.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -1.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -1.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521   -1.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973    0.8166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029083

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15N3O3/c14-10(13(19)16-7-12(17)18)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15H,5,7,14H2,(H,16,19)(H,17,18)

> <INCHI_KEY>
UYKREHOKELZSPB-UHFFFAOYSA-N

> <FORMULA>
C13H15N3O3

> <MOLECULAR_WEIGHT>
261.2765

> <EXACT_MASS>
261.111341361

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.81032131027468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

> <ALOGPS_LOGP>
-0.94

> <JCHEM_LOGP>
-2.1933012878640943

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.474728930085679

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7201495143070713

> <JCHEM_PKA_STRONGEST_BASIC>
7.9595349763807

> <JCHEM_POLAR_SURFACE_AREA>
108.21000000000001

> <JCHEM_REFRACTIVITY>
69.0063

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247340
     RDKit          3D
Tryptophylglycine
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.0126    0.0539    1.4261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.7181    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486   -0.2371   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.4359    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.9773    1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -0.9681    1.8944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188   -0.4357    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9799   -0.1748    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4393    0.3974   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    0.7376   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2238    0.4854   -1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -0.0949   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.6668   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290   -1.2666   -1.6392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    0.0777   -0.0049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563    0.1582   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    0.9844    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221    1.5247    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7982    1.2014   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.3634    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.0389    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -1.8032    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.8411   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332   -0.7694   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634   -1.3576    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342   -1.3201    2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6231   -0.4518    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5165    0.5935   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993    1.1807   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.7375   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    0.5824    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6840   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752   -0.8589   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8623    1.6208   -1.3416 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 12  4  1  0
 12  7  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      -0.459   0.754   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.793   1.524   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.793   3.064   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.127   0.754   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.127  -0.786   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -4.460   1.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.794   0.754   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.201   1.381   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -8.231   0.236   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -7.461  -1.097   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.955  -0.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.925  -1.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.400  -3.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.907  -3.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.937  -2.562   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.874   1.524   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.208   0.754   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.542   1.524   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.208  -0.786   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    1   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0247340
HETATM    1  N1  UNL     1       1.013   0.054   1.426  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.926  -0.718   0.201  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.249  -0.237  -0.582  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.472  -0.436   0.249  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.586  -0.977   1.513  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.895  -0.968   1.894  1.00  0.00           N  
HETATM    7  C5  UNL     1      -3.619  -0.436   0.908  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.980  -0.175   0.734  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.439   0.397  -0.425  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.588   0.738  -1.459  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.224   0.485  -1.305  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.775  -0.095  -0.125  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.195  -0.667  -0.544  1.00  0.00           C  
HETATM   14  O1  UNL     1       2.329  -1.267  -1.639  1.00  0.00           O  
HETATM   15  N3  UNL     1       3.282   0.078  -0.005  1.00  0.00           N  
HETATM   16  C12 UNL     1       4.556   0.158  -0.704  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.510   0.984   0.062  1.00  0.00           C  
HETATM   18  O2  UNL     1       5.222   1.525   1.161  1.00  0.00           O  
HETATM   19  O3  UNL     1       6.798   1.201  -0.416  1.00  0.00           O  
HETATM   20  H1  UNL     1       1.698  -0.363   2.067  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.211   1.039   1.159  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.741  -1.803   0.430  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.094   0.841  -0.824  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.333  -0.769  -1.567  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.763  -1.358   2.121  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.234  -1.320   2.798  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.623  -0.452   1.560  1.00  0.00           H  
HETATM   28  H9  UNL     1      -6.517   0.594  -0.540  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.999   1.181  -2.339  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.538   0.737  -2.088  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.185   0.582   0.907  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.425   0.684  -1.695  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.975  -0.859  -0.825  1.00  0.00           H  
HETATM   34  H15 UNL     1       6.862   1.621  -1.342  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   13   22
CONECT    3    4   23   24
CONECT    4    5    5   12
CONECT    5    6   25
CONECT    6    7   26
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   13   14   14   15
CONECT   15   16   31
CONECT   16   17   32   33
CONECT   17   18   18   19
CONECT   19   34
END

HMDB0247340
     RDKit          3D
Tryptophylglycine
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.0126    0.0539    1.4261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9263   -0.7181    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486   -0.2371   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.4359    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.9773    1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -0.9681    1.8944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188   -0.4357    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9799   -0.1748    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4393    0.3974   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    0.7376   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2238    0.4854   -1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -0.0949   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949   -0.6668   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290   -1.2666   -1.6392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    0.0777   -0.0049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563    0.1582   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    0.9844    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2221    1.5247    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7982    1.2014   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.3634    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.0389    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -1.8032    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.8411   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332   -0.7694   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634   -1.3576    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342   -1.3201    2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6231   -0.4518    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5165    0.5935   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993    1.1807   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.7375   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    0.5824    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6840   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752   -0.8589   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8623    1.6208   -1.3416 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 12  4  1  0
 12  7  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Tryptophyl-L-glycine	HMDB
TRP-Gly	HMDB
Tryptophan glycine dipeptide	HMDB
Tryptophan-glycine dipeptide	HMDB
W-g Dipeptide	HMDB
WG Dipeptide	HMDB
Tryptophanylglycine	HMDB
2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}acetate	HMDB
Tryptophylglycine	HMDB

Chemical Formula

C₁₃H₁₅N₃O₃

Average Molecular Weight

261.2765

Monoisotopic Molecular Weight

261.111341361

IUPAC Name

2-[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

Traditional Name

[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

CAS Registry Number

Not Available

SMILES

NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C13H15N3O3/c14-10(13(19)16-7-12(17)18)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15H,5,7,14H2,(H,16,19)(H,17,18)

InChI Key

UYKREHOKELZSPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Fatty amide
Substituted pyrrole
Fatty acyl
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 25037050)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	-2.19	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	-2.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.01 m³·mol⁻¹	ChemAxon
Polarizability	26.81 Å³	ChemAxon
Number of Rings	2	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]+	159.274	31661259
DarkChem	[M-H]-	159.254	31661259
DeepCCS	[M+H]+	155.207	30932474
DeepCCS	[M-H]-	152.814	30932474
DeepCCS	[M-2H]-	185.7	30932474
DeepCCS	[M+Na]+	161.266	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.1	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tryptophyl-Glycine	NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O	3942.4	Standard polar	33892256
Tryptophyl-Glycine	NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O	2329.6	Standard non polar	33892256
Tryptophyl-Glycine	NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O	2844.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tryptophyl-Glycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=C[NH]C2=CC=CC=C12	2711.6	Semi standard non polar	33892256
Tryptophyl-Glycine,1TMS,isomer #2	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O	2802.1	Semi standard non polar	33892256
Tryptophyl-Glycine,1TMS,isomer #3	C[Si](C)(C)N1C=C(CC(N)C(=O)NCC(=O)O)C2=CC=CC=C21	2738.3	Semi standard non polar	33892256
Tryptophyl-Glycine,1TMS,isomer #4	C[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=C[NH]C2=CC=CC=C12	2771.1	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C	2712.3	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C	2596.6	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2712.6	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2619.6	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #3	C[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2690.7	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #3	C[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2576.3	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #4	C[Si](C)(C)N(C(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C	2887.9	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #4	C[Si](C)(C)N(C(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C	2677.1	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #5	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O	2769.8	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #5	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O	2602.9	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #6	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C	2767.9	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #6	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C	2639.6	Standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #7	C[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2727.7	Semi standard non polar	33892256
Tryptophyl-Glycine,2TMS,isomer #7	C[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2652.3	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2837.1	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2740.8	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #2	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C	2700.0	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #2	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C	2649.1	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #3	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2716.8	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #3	C[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2703.2	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #4	C[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2678.1	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #4	C[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2674.3	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #5	C[Si](C)(C)N(C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C	2862.9	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #5	C[Si](C)(C)N(C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C	2745.3	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #6	C[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2875.8	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #6	C[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2794.8	Standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #7	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C	2740.0	Semi standard non polar	33892256
Tryptophyl-Glycine,3TMS,isomer #7	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C	2724.6	Standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2862.1	Semi standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2841.1	Standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2827.1	Semi standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2788.0	Standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #3	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2707.2	Semi standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #3	C[Si](C)(C)NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2732.5	Standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #4	C[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2891.0	Semi standard non polar	33892256
Tryptophyl-Glycine,4TMS,isomer #4	C[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2861.5	Standard non polar	33892256
Tryptophyl-Glycine,5TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2894.5	Semi standard non polar	33892256
Tryptophyl-Glycine,5TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2879.7	Standard non polar	33892256
Tryptophyl-Glycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=C[NH]C2=CC=CC=C12	3015.3	Semi standard non polar	33892256
Tryptophyl-Glycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O	3050.6	Semi standard non polar	33892256
Tryptophyl-Glycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CC(N)C(=O)NCC(=O)O)C2=CC=CC=C21	3004.5	Semi standard non polar	33892256
Tryptophyl-Glycine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=C[NH]C2=CC=CC=C12	3043.0	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3229.1	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3030.7	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3234.9	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3040.9	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3203.1	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2990.3	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C	3389.9	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CC1=C[NH]C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C	3078.6	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O	3222.9	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O	3021.2	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3269.5	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3062.7	Standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3234.1	Semi standard non polar	33892256
Tryptophyl-Glycine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3031.8	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3584.1	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3329.8	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3347.8	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3247.3	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3449.1	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=C[NH]C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3316.1	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3373.3	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3248.9	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C	3573.1	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C	3303.2	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3599.4	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3384.4	Standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3439.5	Semi standard non polar	33892256
Tryptophyl-Glycine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3295.0	Standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3778.2	Semi standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3588.8	Standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3688.5	Semi standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3497.1	Standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3546.8	Semi standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3480.1	Standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3757.3	Semi standard non polar	33892256
Tryptophyl-Glycine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3545.2	Standard non polar	33892256
Tryptophyl-Glycine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3927.3	Semi standard non polar	33892256
Tryptophyl-Glycine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3719.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kcr-7920000000-7ffae3b7fdea43455194	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-3930000000-2f12409e9669b0a762dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophyl-Glycine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	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 - Tryptophyl-Glycine 10V, Positive-QTOF	splash10-074i-8590000000-8dd1c8ee15ff1e8225bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 20V, Positive-QTOF	splash10-00fr-9400000000-7d57f8e31d397ed2aa46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 40V, Positive-QTOF	splash10-05ec-9600000000-30b80d7ce818885b2635	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 10V, Negative-QTOF	splash10-03di-0190000000-c9b80b0287438ae1354a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 20V, Negative-QTOF	splash10-03k9-6490000000-1fe7f9b359e0c29d1f27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 40V, Negative-QTOF	splash10-00di-9500000000-a7a32c4036d3ad636d8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 10V, Negative-QTOF	splash10-03di-1290000000-bf100e30ff58bbb8ab6b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 20V, Negative-QTOF	splash10-00ri-9720000000-d242ffb6ee817b3be4e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 40V, Negative-QTOF	splash10-0600-9500000000-598f8103041677f61792	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 10V, Positive-QTOF	splash10-03di-0390000000-93faef45e80033318f73	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 20V, Positive-QTOF	splash10-0006-1910000000-2b920e06645b8a8baff7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophyl-Glycine 40V, Positive-QTOF	splash10-0006-2900000000-6d130cde240d8a461990	2021-09-24	Wishart Lab	View Spectrum

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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112088

KNApSAcK ID

Not Available

Chemspider ID

231453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

263471

PDB ID

Not Available

ChEBI ID

Not Available

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

Eisenberg AS, Juszczak LJ: Correlation of TrpGly and GlyTrp Rotamer Structure with W7 and W10 UV Resonance Raman Modes and Fluorescence Emission Shifts. J Amino Acids. 2012;2012:735076. doi: 10.1155/2012/735076. Epub 2012 Jul 22. [PubMed:22888404 ]
Pan Y, Birkedal H, Pattison P, Brown D, Chapuis G: Molecular dynamics study of tryptophylglycine: a dipeptide nanotube with confined water. J Phys Chem B. 2004 May 20;108(20):6458-66. doi: 10.1021/jp037219v. [PubMed:18950135 ]
Yajima H, Kubo K: Studies on peptides. IV. The synthesis of D-histidyl-L-phenylalanyl-L- arginyl-L-tryptophylglycine and L-histidyl-L-phenylalanyl-L-arginyl-D-tryptophylglycine and their physiological properties in frog melanocyte in vitro. Chem Pharm Bull (Tokyo). 1965 Jul;13(7):759-64. [PubMed:5879901 ]
YAJIMA H, KUBO K: THE SYNTHESIS OF D-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYLGLYCINE AND L-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-D-TRYPTOPHYLGLYCINE AND THEIR PHYSIOLOGICAL PROPERTIES IN FROG MELANOCYTE. Biochim Biophys Acta. 1965 Mar 8;97:596-7. [PubMed:14323609 ]
Partanen S, Kaakkola S, Kaariainen I: Tryptophylglycine dipeptide in ACTH/MSH cells of the human hypophysis: its identification and studies on its antinociceptive effects in mice. Acta Physiol Scand. 1979 Nov;107(3):213-18. [PubMed:231893 ]
YAJIMA H, KUBO K: STUDIES ON PEPTIDES. II. SYNTHESIS AND PHYSIOLOGICAL PROPERTIES OF D-HISTIDYL-D-PHENYLALANYL-D-ARGINYL-D-TRYPTOPHYLGLYCINE, AN OPTICAL ANTIPODE OF AN ACTIVE FRAGMENT OF ALPHA-MELANOCYTE-STIMULATING HORMONE. J Am Chem Soc. 1965 May 5;87:2039-44. [PubMed:14290281 ]
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Showing metabocard for Tryptophyl-Glycine (HMDB0029083)

MOL for HMDB0029083 (Tryptophyl-Glycine)

3D MOL for HMDB0029083 (Tryptophyl-Glycine)

3D SDF for HMDB0029083 (Tryptophyl-Glycine)

3D-SDF for HMDB0029083 (Tryptophyl-Glycine)

PDB for HMDB0029083 (Tryptophyl-Glycine)

3D PDB for HMDB0029083 (Tryptophyl-Glycine)

SMILES for HMDB0029083 (Tryptophyl-Glycine)

INCHI for HMDB0029083 (Tryptophyl-Glycine)

Structure for HMDB0029083 (Tryptophyl-Glycine)

3D Structure for HMDB0029083 (Tryptophyl-Glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra