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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:43:25 UTC

Update Date

2021-09-26 23:04:24 UTC

HMDB ID

HMDB0252047

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ethyl L-tryptophanate

Description

ethyl tryptophanate, also known as tryptophan ethyl ester, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review very few articles have been published on ethyl tryptophanate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl l-tryptophanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl L-tryptophanate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252047
     RDKit          3D
Ethyl L-tryptophanate
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9514    0.8698    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802    1.5461   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    1.0188   -0.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    1.0465    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    1.5670    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    0.4638   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.0701   -1.7153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.6621    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -1.1888   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -2.3515   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -2.4416   -1.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.3797   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5367   -0.9821   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8693    0.1948    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    1.0069    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    0.5981    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5791    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    1.2667    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -0.2335    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0496    1.0275    0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    1.3427   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.6297   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0556    1.2373   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349    0.6530   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -0.6824   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414   -1.4279    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.1873    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -3.0560   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9643   -3.2335   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2315   -1.6301   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    0.5053    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343    1.9437    1.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    1.1883    1.1829 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

  Mrv1533004251512112D          

 17 18  0  0  0  0            999 V2000
    4.8525   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -2.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.0261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2256   -0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326    0.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451   -0.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2521   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5070   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930   -1.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252047

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C(N)CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2/c1-2-17-13(16)11(14)7-9-8-15-12-6-4-3-5-10(9)12/h3-6,8,11,15H,2,7,14H2,1H3

> <INCHI_KEY>
DABYEOZXRSTEGL-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O2

> <MOLECULAR_WEIGHT>
232.283

> <EXACT_MASS>
232.121177763

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.164072833688643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-amino-3-(1H-indol-3-yl)propanoate

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.6790790566666662

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.145669643014518

> <JCHEM_PKA_STRONGEST_BASIC>
6.91712755984729

> <JCHEM_POLAR_SURFACE_AREA>
68.11

> <JCHEM_REFRACTIVITY>
65.7205

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-amino-3-(1H-indol-3-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252047
     RDKit          3D
Ethyl L-tryptophanate
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9514    0.8698    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802    1.5461   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    1.0188   -0.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    1.0465    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    1.5670    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    0.4638   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.0701   -1.7153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.6621    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -1.1888   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -2.3515   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -2.4416   -1.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.3797   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5367   -0.9821   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8693    0.1948    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    1.0069    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    0.5981    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5791    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    1.2667    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -0.2335    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0496    1.0275    0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    1.3427   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.6297   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0556    1.2373   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349    0.6530   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -0.6824   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414   -1.4279    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.1873    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -3.0560   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9643   -3.2335   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2315   -1.6301   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    0.5053    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343    1.9437    1.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    1.1883    1.1829 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.058  -1.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.392  -2.359   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.725  -1.589   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      13.059  -2.359   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.059  -3.899   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.393  -1.589   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      14.393  -0.049   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.060  -1.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.221  -0.057   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      18.727   0.263   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      19.497  -1.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.004  -1.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.480  -2.856   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.449  -4.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.943  -3.680   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.467  -2.215   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0252047
HETATM    1  C1  UNL     1       4.951   0.870   0.797  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.380   1.546  -0.443  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.122   1.019  -0.774  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.023   1.047   0.051  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.112   1.567   1.178  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.751   0.464  -0.397  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.906  -0.070  -1.715  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.281  -0.662   0.504  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.004  -1.189  -0.021  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.233  -2.351  -0.723  1.00  0.00           C  
HETATM   11  N2  UNL     1      -2.543  -2.442  -1.004  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.206  -1.380  -0.517  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.537  -0.982  -0.524  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.869   0.195   0.088  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.943   1.007   0.713  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.631   0.598   0.711  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.261  -0.579   0.105  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.466   1.267   1.710  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.807  -0.233   0.705  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.050   1.027   0.805  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.065   1.343  -1.300  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.273   2.630  -0.266  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.056   1.237  -0.455  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.835   0.653  -2.466  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.740  -0.682  -1.834  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.041  -1.428   0.635  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.115  -0.187   1.516  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.442  -3.056  -0.985  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.964  -3.234  -1.529  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.232  -1.630  -1.015  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.907   0.505   0.083  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.234   1.944   1.194  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.856   1.188   1.183  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   23
CONECT    7   24   25
CONECT    8    9   26   27
CONECT    9   10   10   17
CONECT   10   11   28
CONECT   11   12   29
CONECT   12   13   13   17
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   33
END

HMDB0252047
     RDKit          3D
Ethyl L-tryptophanate
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9514    0.8698    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802    1.5461   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    1.0188   -0.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    1.0465    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    1.5670    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    0.4638   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.0701   -1.7153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808   -0.6621    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -1.1888   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -2.3515   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -2.4416   -1.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.3797   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5367   -0.9821   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8693    0.1948    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    1.0069    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    0.5981    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5791    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    1.2667    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -0.2335    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0496    1.0275    0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    1.3427   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732    2.6297   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0556    1.2373   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349    0.6530   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -0.6824   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414   -1.4279    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -0.1873    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418   -3.0560   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9643   -3.2335   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2315   -1.6301   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    0.5053    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343    1.9437    1.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    1.1883    1.1829 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl tryptophanic acid	Generator
Tryptophan ethyl ester	MeSH
Tryptophan ethyl ester monohydrochloride, (DL)-isomer	MeSH
Tryptophan ethyl ester monohydrochloride, (L)-isomer	MeSH
Tryptophan ethyl ester monotosylate, (L)-isomer	MeSH
Tryptophan ethyl ester, (L)-isomer	MeSH
Tryptophan ethyl ester, alpha-14C-labeled CPD (DL)-isomer	MeSH
Ethyl 2-amino-3-(1H-indol-3-yl)propanoic acid	Generator

Chemical Formula

C₁₃H₁₆N₂O₂

Average Molecular Weight

232.283

Monoisotopic Molecular Weight

232.121177763

IUPAC Name

ethyl 2-amino-3-(1H-indol-3-yl)propanoate

Traditional Name

ethyl 2-amino-3-(1H-indol-3-yl)propanoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C(N)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C13H16N2O2/c1-2-17-13(16)11(14)7-9-8-15-12-6-4-3-5-10(9)12/h3-6,8,11,15H,2,7,14H2,1H3

InChI Key

DABYEOZXRSTEGL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

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 acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.79	ALOGPS
logP	1.68	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	16.15	ChemAxon
pKa (Strongest Basic)	6.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	65.72 m³·mol⁻¹	ChemAxon
Polarizability	25.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	183.617	30932474
DeepCCS	[M+Na]+	158.725	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.8	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl L-tryptophanate	CCOC(=O)C(N)CC1=CNC2=CC=CC=C12	3235.7	Standard polar	33892256
Ethyl L-tryptophanate	CCOC(=O)C(N)CC1=CNC2=CC=CC=C12	1874.5	Standard non polar	33892256
Ethyl L-tryptophanate	CCOC(=O)C(N)CC1=CNC2=CC=CC=C12	2156.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl L-tryptophanate,1TMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2176.8	Semi standard non polar	33892256
Ethyl L-tryptophanate,1TMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2118.5	Standard non polar	33892256
Ethyl L-tryptophanate,1TMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2867.4	Standard polar	33892256
Ethyl L-tryptophanate,1TMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2171.4	Semi standard non polar	33892256
Ethyl L-tryptophanate,1TMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2154.2	Standard non polar	33892256
Ethyl L-tryptophanate,1TMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2971.4	Standard polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2206.7	Semi standard non polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2208.9	Standard non polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2617.9	Standard polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2382.4	Semi standard non polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2277.8	Standard non polar	33892256
Ethyl L-tryptophanate,2TMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2734.0	Standard polar	33892256
Ethyl L-tryptophanate,3TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2444.0	Semi standard non polar	33892256
Ethyl L-tryptophanate,3TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2345.0	Standard non polar	33892256
Ethyl L-tryptophanate,3TMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2562.1	Standard polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2414.4	Semi standard non polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2333.1	Standard non polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #1	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2933.8	Standard polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2401.0	Semi standard non polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2358.1	Standard non polar	33892256
Ethyl L-tryptophanate,1TBDMS,isomer #2	CCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3021.8	Standard polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2618.1	Semi standard non polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2628.0	Standard non polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #1	CCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2810.0	Standard polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2834.2	Semi standard non polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2690.5	Standard non polar	33892256
Ethyl L-tryptophanate,2TBDMS,isomer #2	CCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2860.4	Standard polar	33892256
Ethyl L-tryptophanate,3TBDMS,isomer #1	CCOC(=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	3051.5	Semi standard non polar	33892256
Ethyl L-tryptophanate,3TBDMS,isomer #1	CCOC(=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	2917.5	Standard non polar	33892256
Ethyl L-tryptophanate,3TBDMS,isomer #1	CCOC(=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	2817.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl L-tryptophanate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-09061ada18540590919b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl L-tryptophanate 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 - Ethyl L-tryptophanate 10V, Positive-QTOF	splash10-001i-0590000000-d97fd41a2ea8ff7e7f90	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl L-tryptophanate 20V, Positive-QTOF	splash10-001i-0900000000-4db1122e377d17b313eb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl L-tryptophanate 40V, Positive-QTOF	splash10-015c-2900000000-d2266fecc87960914041	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl L-tryptophanate 10V, Negative-QTOF	splash10-001i-1390000000-525bf26fe595d98fa6c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl L-tryptophanate 20V, Negative-QTOF	splash10-01c0-7910000000-b5cf41860a7e352d94b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl L-tryptophanate 40V, Negative-QTOF	splash10-00ke-7900000000-d26ded742076f458f6cc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

118571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134520

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Ethyl L-tryptophanate (HMDB0252047)

MOL for HMDB0252047 (Ethyl L-tryptophanate)

3D MOL for HMDB0252047 (Ethyl L-tryptophanate)

3D SDF for HMDB0252047 (Ethyl L-tryptophanate)

3D-SDF for HMDB0252047 (Ethyl L-tryptophanate)

PDB for HMDB0252047 (Ethyl L-tryptophanate)

3D PDB for HMDB0252047 (Ethyl L-tryptophanate)

SMILES for HMDB0252047 (Ethyl L-tryptophanate)

INCHI for HMDB0252047 (Ethyl L-tryptophanate)

Structure for HMDB0252047 (Ethyl L-tryptophanate)

3D Structure for HMDB0252047 (Ethyl L-tryptophanate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra