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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:35:06 UTC

Update Date

2021-09-26 23:09:33 UTC

HMDB ID

HMDB0255052

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetyl-D-tryptophan

Description

N-acetyltryptophan belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acetyltryptophan is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on N-acetyltryptophan. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-acetyl-d-tryptophan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Acetyl-D-tryptophan 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

HMDB0255052
     RDKit          3D
N-Acetyl-D-tryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0198    0.9032   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934   -0.4889   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7690   -1.2337   -1.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -1.0800   -0.4364 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -0.7011    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306    0.5419   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.7860   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    1.7143    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.6173    1.1433 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    0.6422    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.1336    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3562   -0.8889   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282   -1.3931   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471   -0.9048   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    0.1169   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -0.6408    1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406   -0.8595    2.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.3525    2.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    0.9655    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    1.5206   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    1.2999    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942   -1.7980   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -1.5337   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017    1.4564   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380    0.3816   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    2.4144    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    2.1844    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394    0.5348    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -1.2672   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -2.1942   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.3277   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -0.5489    3.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END


  Mrv1652305152108282D          

 18 19  0  0  0  0            999 V2000
   -1.2400   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -0.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    1.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  4  0  0  0
 16  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255052

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)

> <INCHI_KEY>
DZTHIGRZJZPRDV-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.266

> <EXACT_MASS>
246.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.169450863977346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
1.8148277759999996

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.258324721897573

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.170412374563318

> <JCHEM_PKA_STRONGEST_BASIC>
1.5194234386666143

> <JCHEM_POLAR_SURFACE_AREA>
85.67999999999999

> <JCHEM_REFRACTIVITY>
66.16830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255052
     RDKit          3D
N-Acetyl-D-tryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0198    0.9032   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934   -0.4889   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7690   -1.2337   -1.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -1.0800   -0.4364 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -0.7011    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306    0.5419   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.7860   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    1.7143    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.6173    1.1433 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    0.6422    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.1336    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3562   -0.8889   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282   -1.3931   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471   -0.9048   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    0.1169   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -0.6408    1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406   -0.8595    2.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.3525    2.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    0.9655    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    1.5206   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    1.2999    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942   -1.7980   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -1.5337   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017    1.4564   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380    0.3816   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    2.4144    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    2.1844    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394    0.5348    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -1.2672   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -2.1942   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.3277   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -0.5489    3.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -2.315  -3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.839  -1.973   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.887   0.957   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -0.333  -1.652   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.869  -0.828   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.393   0.636   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.411   2.421   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   14                                                       
CONECT    8    1   15   16                                                  
CONECT    9    6    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    5   10   14                                                  
CONECT   12    6   13   15                                                  
CONECT   13   12   17   18                                                  
CONECT   14    7   11                                                       
CONECT   15    8   12                                                       
CONECT   16    8                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0255052
HETATM    1  C1  UNL     1      -4.020   0.903  -0.132  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.693  -0.489  -0.511  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.769  -1.234  -1.019  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.591  -1.080  -0.436  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.310  -0.701   0.001  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.731   0.542  -0.622  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.622   0.786  -0.058  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.988   1.714   0.898  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.298   1.617   1.143  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.834   0.642   0.374  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.100   0.134   0.220  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.356  -0.889  -0.671  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.328  -1.393  -1.404  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.047  -0.905  -1.272  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.804   0.117  -0.379  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.287  -0.641   1.496  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.341  -0.859   2.149  1.00  0.00           O  
HETATM   18  O3  UNL     1      -0.152  -0.353   2.233  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.095   0.965   0.179  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.960   1.521  -1.069  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.399   1.300   0.690  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.694  -1.798  -1.841  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.595  -1.534  -0.266  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.302   1.456  -0.449  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.638   0.382  -1.709  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.323   2.414   1.382  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.852   2.184   1.817  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.939   0.535   0.811  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.369  -1.267  -0.764  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.493  -2.194  -2.109  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.244  -1.328  -1.875  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.023  -0.549   3.195  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22
CONECT    4    5
CONECT    5    6   16   23
CONECT    6    7   24   25
CONECT    7    8    8   15
CONECT    8    9   26
CONECT    9   10   27
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   16   17   17   18
CONECT   18   32
END

HMDB0255052
     RDKit          3D
N-Acetyl-D-tryptophan
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0198    0.9032   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934   -0.4889   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7690   -1.2337   -1.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -1.0800   -0.4364 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -0.7011    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306    0.5419   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.7860   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    1.7143    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.6173    1.1433 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    0.6422    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.1336    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3562   -0.8889   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282   -1.3931   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471   -0.9048   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    0.1169   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -0.6408    1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406   -0.8595    2.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.3525    2.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    0.9655    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    1.5206   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    1.2999    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942   -1.7980   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -1.5337   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017    1.4564   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380    0.3816   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    2.4144    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    2.1844    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394    0.5348    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -1.2672   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4930   -2.1942   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.3277   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -0.5489    3.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acetyltryptophan	ChEBI
N-Acetyl-DL-tryptophan	ChEBI
N-Acetyltryptophane	ChEBI
N-Acetyltryptophan	MeSH
N-Acetyltryptophanate sodium	MeSH
N-Acetyl-D-tryptophan	MeSH

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.266

Monoisotopic Molecular Weight

246.100442319

IUPAC Name

2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC(CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)

InChI Key

DZTHIGRZJZPRDV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acetyl-amino acid (CHEBI:70976 )
tryptophan derivative (CHEBI:70976 )

Ontology

Not Available

Non-excretory biofluid

Blood (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	1.48	ALOGPS
logP	1.81	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.17 m³·mol⁻¹	ChemAxon
Polarizability	25.17 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]-	181.995	30932474
DeepCCS	[M+Na]+	157.336	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.7	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	157.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-D-tryptophan	CC(O)=NC(CC1=CNC2=CC=CC=C12)C(O)=O	3539.2	Standard polar	33892256
N-Acetyl-D-tryptophan	CC(O)=NC(CC1=CNC2=CC=CC=C12)C(O)=O	2176.3	Standard non polar	33892256
N-Acetyl-D-tryptophan	CC(O)=NC(CC1=CNC2=CC=CC=C12)C(O)=O	2401.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-D-tryptophan,3TMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2465.8	Semi standard non polar	33892256
N-Acetyl-D-tryptophan,3TMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2378.7	Standard non polar	33892256
N-Acetyl-D-tryptophan,3TMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2691.2	Standard polar	33892256
N-Acetyl-D-tryptophan,3TBDMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3033.7	Semi standard non polar	33892256
N-Acetyl-D-tryptophan,3TBDMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2975.1	Standard non polar	33892256
N-Acetyl-D-tryptophan,3TBDMS,isomer #1	CC(=NC(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2964.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-8960000000-205ab2bf8689848f53d1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-tryptophan GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 40V, Negative-QTOF	splash10-0600-9300000000-2b3d69bf9a870ff8481e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 20V, Negative-QTOF	splash10-00di-9320000000-b827acad923682cdcaa7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 10V, Positive-QTOF	splash10-0k9i-0950000000-c6bf49fca310d11ad26e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 20V, Positive-QTOF	splash10-0a4r-0900000000-7aea356461a3ed6fd6f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 10V, Negative-QTOF	splash10-0v4j-3290000000-a8a644c6fb68278a8fd8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-tryptophan 40V, Positive-QTOF	splash10-0159-0900000000-e87ebdd971a104fad6c2	2021-09-20	HMDB team, MONA	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

C00047984

Chemspider ID

1925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

70976

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1265471

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 N-Acetyl-D-tryptophan (HMDB0255052)

MOL for HMDB0255052 (N-Acetyl-D-tryptophan)

3D MOL for HMDB0255052 (N-Acetyl-D-tryptophan)

3D SDF for HMDB0255052 (N-Acetyl-D-tryptophan)

3D-SDF for HMDB0255052 (N-Acetyl-D-tryptophan)

PDB for HMDB0255052 (N-Acetyl-D-tryptophan)

3D PDB for HMDB0255052 (N-Acetyl-D-tryptophan)

SMILES for HMDB0255052 (N-Acetyl-D-tryptophan)

INCHI for HMDB0255052 (N-Acetyl-D-tryptophan)

Structure for HMDB0255052 (N-Acetyl-D-tryptophan)

3D Structure for HMDB0255052 (N-Acetyl-D-tryptophan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra