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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:49:51 UTC

Update Date

2021-09-26 23:16:46 UTC

HMDB ID

HMDB0259307

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tryptophan butyl ester

Description

Tryptophan butyl 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 a small amount of articles have been published on Tryptophan butyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tryptophan butyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tryptophan butyl ester 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

HMDB0259307
     RDKit          3D
Tryptophan butyl ester
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.5455   -1.1974   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1971   -1.7375   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179   -0.6562   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.1925    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    0.7888    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    0.6074    0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -0.5200    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    1.7193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    2.8717    1.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352    1.9489   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.7744   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -0.0858   -1.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.0301   -1.8955 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -0.8110   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.4984   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0808    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078    0.0533    1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419    0.7323    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    0.3220   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3265   -1.6140   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501   -1.5230    0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4948   -0.0979   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8894   -2.6325    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2549   -1.9515   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    0.2192   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -1.1084   -0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126   -1.0203    1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9648    0.2734    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.3935    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    3.4713    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.4059    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    2.8139   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    2.1930   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.0701   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -1.8238   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -2.3632   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2314   -1.6520    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6977    0.3586    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    1.6038    1.2836 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

  Mrv1652309112123502D          

 19 20  0  0  0  0            999 V2000
    6.2116   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6405   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -2.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2128   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9273   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0136   -0.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8205   -0.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2330   -1.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0400   -1.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2949   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7429   -2.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9359   -2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6810   -1.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -0.4677    0.0000 N   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 10 18  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259307

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O2/c1-2-3-8-19-15(18)13(16)9-11-10-17-14-7-5-4-6-12(11)14/h4-7,10,13,17H,2-3,8-9,16H2,1H3

> <INCHI_KEY>
YBWXYSUDFGURNJ-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O2

> <MOLECULAR_WEIGHT>
260.337

> <EXACT_MASS>
260.152477892

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.4691493210633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.6461701166666662

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.145669642959405

> <JCHEM_PKA_STRONGEST_BASIC>
6.917122162044883

> <JCHEM_POLAR_SURFACE_AREA>
68.11

> <JCHEM_REFRACTIVITY>
74.8455

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.00e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259307
     RDKit          3D
Tryptophan butyl ester
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.5455   -1.1974   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1971   -1.7375   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179   -0.6562   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.1925    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    0.7888    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    0.6074    0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -0.5200    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    1.7193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    2.8717    1.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352    1.9489   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.7744   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -0.0858   -1.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.0301   -1.8955 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -0.8110   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.4984   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0808    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078    0.0533    1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419    0.7323    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    0.3220   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3265   -1.6140   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501   -1.5230    0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4948   -0.0979   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8894   -2.6325    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2549   -1.9515   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    0.2192   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -1.1084   -0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126   -1.0203    1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9648    0.2734    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.3935    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    3.4713    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.4059    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    2.8139   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    2.1930   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.0701   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -1.8238   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -2.3632   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2314   -1.6520    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6977    0.3586    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    1.6038    1.2836 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      11.595  -2.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.929  -3.183   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.262  -2.413   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.596  -3.183   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.930  -2.413   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      18.263  -3.183   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.263  -4.723   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      19.597  -2.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.931  -3.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.264  -2.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.425  -0.881   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      23.932  -0.561   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      24.702  -1.895   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.208  -2.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.684  -3.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.653  -4.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.147  -4.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.671  -3.039   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      19.597  -0.873   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   10                                                  
CONECT   19    8                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0259307
HETATM    1  C1  UNL     1      -5.546  -1.197  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.197  -1.738  -0.530  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.118  -0.656  -0.387  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.999  -0.192   1.031  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.015   0.789   1.133  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.681   0.607   0.814  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.295  -0.520   0.397  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.297   1.719   0.957  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.388   2.872   1.431  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.035   1.949  -0.343  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.785   0.774  -0.790  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.422  -0.086  -1.803  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.379  -1.030  -1.896  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.336  -0.811  -0.988  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.496  -1.498  -0.709  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.334  -1.081   0.281  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.008   0.053   1.011  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.842   0.732   0.719  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.975   0.322  -0.285  1.00  0.00           C  
HETATM   20  H1  UNL     1      -6.327  -1.614  -0.775  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.750  -1.523   0.949  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.495  -0.098  -0.159  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.889  -2.633   0.018  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.255  -1.952  -1.629  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.388   0.219  -1.006  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.203  -1.108  -0.789  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.813  -1.020   1.746  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.965   0.273   1.317  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.010   1.393   1.765  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.159   3.471   2.081  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.902   3.406   0.703  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.711   2.814  -0.299  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.264   2.193  -1.105  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.549  -0.070  -2.446  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.372  -1.824  -2.583  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.726  -2.363  -1.279  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.231  -1.652   0.465  1.00  0.00           H  
HETATM   38  H19 UNL     1       5.698   0.359   1.791  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.595   1.604   1.284  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   29
CONECT    9   30   31
CONECT   10   11   32   33
CONECT   11   12   12   19
CONECT   12   13   34
CONECT   13   14   35
CONECT   14   15   15   19
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   38
CONECT   18   19   19   39
END

HMDB0259307
     RDKit          3D
Tryptophan butyl ester
 39 40  0  0  0  0  0  0  0  0999 V2000
   -5.5455   -1.1974   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1971   -1.7375   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179   -0.6562   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.1925    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    0.7888    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    0.6074    0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -0.5200    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    1.7193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    2.8717    1.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0352    1.9489   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.7744   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -0.0858   -1.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.0301   -1.8955 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -0.8110   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.4984   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0808    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078    0.0533    1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419    0.7323    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    0.3220   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3265   -1.6140   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501   -1.5230    0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4948   -0.0979   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8894   -2.6325    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2549   -1.9515   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    0.2192   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027   -1.1084   -0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126   -1.0203    1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9648    0.2734    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.3935    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    3.4713    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    3.4059    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    2.8139   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    2.1930   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.0701   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -1.8238   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -2.3632   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2314   -1.6520    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6977    0.3586    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    1.6038    1.2836 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butyl 2-amino-3-(1H-indol-3-yl)propanoic acid	HMDB

Chemical Formula

C₁₅H₂₀N₂O₂

Average Molecular Weight

260.337

Monoisotopic Molecular Weight

260.152477892

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H20N2O2/c1-2-3-8-19-15(18)13(16)9-11-10-17-14-7-5-4-6-12(11)14/h4-7,10,13,17H,2-3,8-9,16H2,1H3

InChI Key

YBWXYSUDFGURNJ-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	2.45	ALOGPS
logP	2.65	ChemAxon
logS	-3.5	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	7	ChemAxon
Refractivity	74.85 m³·mol⁻¹	ChemAxon
Polarizability	29.47 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]-	194.48	30932474
DeepCCS	[M+Na]+	170.276	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.8	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	165.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tryptophan butyl ester	CCCCOC(=O)C(N)CC1=CNC2=CC=CC=C12	3398.6	Standard polar	33892256
Tryptophan butyl ester	CCCCOC(=O)C(N)CC1=CNC2=CC=CC=C12	2000.0	Standard non polar	33892256
Tryptophan butyl ester	CCCCOC(=O)C(N)CC1=CNC2=CC=CC=C12	2321.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tryptophan butyl ester,1TMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2348.9	Semi standard non polar	33892256
Tryptophan butyl ester,1TMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	2308.1	Standard non polar	33892256
Tryptophan butyl ester,1TMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C	3031.3	Standard polar	33892256
Tryptophan butyl ester,1TMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2353.1	Semi standard non polar	33892256
Tryptophan butyl ester,1TMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2323.4	Standard non polar	33892256
Tryptophan butyl ester,1TMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	3158.9	Standard polar	33892256
Tryptophan butyl ester,2TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2373.7	Semi standard non polar	33892256
Tryptophan butyl ester,2TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2395.5	Standard non polar	33892256
Tryptophan butyl ester,2TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C	2800.0	Standard polar	33892256
Tryptophan butyl ester,2TMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2548.1	Semi standard non polar	33892256
Tryptophan butyl ester,2TMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2468.7	Standard non polar	33892256
Tryptophan butyl ester,2TMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2906.0	Standard polar	33892256
Tryptophan butyl ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2607.3	Semi standard non polar	33892256
Tryptophan butyl ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2533.1	Standard non polar	33892256
Tryptophan butyl ester,3TMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2736.9	Standard polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2585.2	Semi standard non polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2530.8	Standard non polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #1	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	3097.9	Standard polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2563.3	Semi standard non polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2533.8	Standard non polar	33892256
Tryptophan butyl ester,1TBDMS,isomer #2	CCCCOC(=O)C(N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3209.3	Standard polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2777.8	Semi standard non polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2807.4	Standard non polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #1	CCCCOC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N[Si](C)(C)C(C)(C)C	2980.9	Standard polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3010.9	Semi standard non polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2883.2	Standard non polar	33892256
Tryptophan butyl ester,2TBDMS,isomer #2	CCCCOC(=O)C(CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3030.0	Standard polar	33892256
Tryptophan butyl ester,3TBDMS,isomer #1	CCCCOC(=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	3231.7	Semi standard non polar	33892256
Tryptophan butyl ester,3TBDMS,isomer #1	CCCCOC(=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	3087.5	Standard non polar	33892256
Tryptophan butyl ester,3TBDMS,isomer #1	CCCCOC(=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	2971.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophan butyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-d707f657c5bb4b19048c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophan butyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

364180

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

411386

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 Tryptophan butyl ester (HMDB0259307)

MOL for HMDB0259307 (Tryptophan butyl ester)

3D MOL for HMDB0259307 (Tryptophan butyl ester)

3D SDF for HMDB0259307 (Tryptophan butyl ester)

3D-SDF for HMDB0259307 (Tryptophan butyl ester)

PDB for HMDB0259307 (Tryptophan butyl ester)

3D PDB for HMDB0259307 (Tryptophan butyl ester)

SMILES for HMDB0259307 (Tryptophan butyl ester)

INCHI for HMDB0259307 (Tryptophan butyl ester)

Structure for HMDB0259307 (Tryptophan butyl ester)

3D Structure for HMDB0259307 (Tryptophan butyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra