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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:08:38 UTC

Update Date

2021-09-26 22:51:19 UTC

HMDB ID

HMDB0243932

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indoximod

Description

1-methyltryptophan belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Based on a literature review a significant number of articles have been published on 1-methyltryptophan. This compound has been identified in human blood as reported by (PMID: 31557052 ). Indoximod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Indoximod 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

HMDB0243932
     RDKit          3D
Indoximod
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.8395   -2.5494    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -1.2239    0.0552 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.0362   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.3258   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176    1.1004   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.3197   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302   -0.5601   -1.2609 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -0.4014    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802    0.1709    2.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079   -1.7330    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    0.9321    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.2458    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    2.5533    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7052    1.5544    0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707    0.2542    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.0544    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005   -3.1906   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -2.5009    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -3.0086    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -1.7844   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    1.7394    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.7990   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051    1.0859   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186   -0.3212   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019   -1.5469   -0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470   -2.0581    0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    3.0474    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244    3.5783    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    1.8045    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -0.5422    0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  2  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv1533004241509452D          

 16 17  0  0  0  0            999 V2000
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    2.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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
    2.6378   -1.5229    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  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
  2 16  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243932

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=C(CC(N)C(O)=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)

> <INCHI_KEY>
ZADWXFSZEAPBJS-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.256

> <EXACT_MASS>
218.105527699

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.367171511114556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-0.8616843853371201

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5847882143776375

> <JCHEM_PKA_STRONGEST_BASIC>
9.393174267259962

> <JCHEM_POLAR_SURFACE_AREA>
68.25

> <JCHEM_REFRACTIVITY>
61.09950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyltryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243932
     RDKit          3D
Indoximod
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.8395   -2.5494    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -1.2239    0.0552 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.0362   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.3258   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176    1.1004   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.3197   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302   -0.5601   -1.2609 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -0.4014    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802    0.1709    2.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079   -1.7330    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    0.9321    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.2458    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    2.5533    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7052    1.5544    0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707    0.2542    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.0544    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005   -3.1906   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -2.5009    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -3.0086    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -1.7844   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    1.7394    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.7990   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051    1.0859   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186   -0.3212   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019   -1.5469   -0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470   -2.0581    0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    3.0474    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244    3.5783    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    1.8045    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -0.5422    0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  2  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.887   0.583   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.839   3.513   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.698   4.337   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0243932
HETATM    1  C1  UNL     1      -1.839  -2.549   0.093  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.236  -1.224   0.055  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.085  -1.036  -0.016  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.272   0.326  -0.032  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.518   1.100  -0.101  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.772   0.320  -0.165  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.930  -0.560  -1.261  1.00  0.00           N  
HETATM    8  C6  UNL     1       3.055  -0.401   1.095  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.980   0.171   2.205  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.408  -1.733   1.034  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.964   0.932   0.032  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.413   2.246   0.051  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.755   2.553   0.121  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.705   1.554   0.176  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.271   0.254   0.158  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.919  -0.054   0.087  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.500  -3.191  -0.740  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.951  -2.501   0.054  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.519  -3.009   1.065  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.882  -1.784  -0.056  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.556   1.739   0.808  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.448   1.799  -0.962  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.605   1.086  -0.248  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.719  -0.321  -1.897  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.102  -1.547  -0.937  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.347  -2.058   0.781  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.711   3.047   0.010  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.124   3.578   0.137  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.781   1.805   0.233  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.988  -0.542   0.200  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16
CONECT    3    4    4   20
CONECT    4    5   11
CONECT    5    6   21   22
CONECT    6    7    8   23
CONECT    7   24   25
CONECT    8    9    9   10
CONECT   10   26
CONECT   11   12   12   16
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   29
CONECT   15   16   16   30
END

HMDB0243932
     RDKit          3D
Indoximod
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.8395   -2.5494    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -1.2239    0.0552 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.0362   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.3258   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176    1.1004   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.3197   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302   -0.5601   -1.2609 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -0.4014    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802    0.1709    2.2046 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079   -1.7330    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    0.9321    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135    2.2458    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    2.5533    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7052    1.5544    0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707    0.2542    0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194   -0.0544    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005   -3.1906   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -2.5009    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -3.0086    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -1.7844   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    1.7394    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.7990   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051    1.0859   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186   -0.3212   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019   -1.5469   -0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470   -2.0581    0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    3.0474    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244    3.5783    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    1.8045    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9876   -0.5422    0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  2  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methyl-DL-tryptophan	ChEBI
N-Methyl-DL-tryptophan	ChEBI
N-Methyltryptophan	ChEBI

Chemical Formula

C₁₂H₁₄N₂O₂

Average Molecular Weight

218.256

Monoisotopic Molecular Weight

218.105527699

IUPAC Name

2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid

Traditional Name

1-methyltryptophan

CAS Registry Number

Not Available

SMILES

CN1C=C(CC(N)C(O)=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)

InChI Key

ZADWXFSZEAPBJS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:72821 )
tryptophan derivative (CHEBI:72821 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

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	-0.82	ALOGPS
logP	-0.86	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.1 m³·mol⁻¹	ChemAxon
Polarizability	23.37 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
DeepCCS	[M-2H]-	179.064	30932474
DeepCCS	[M+Na]+	153.706	30932474
AllCCS	[M+H]+	151.3	32859911
AllCCS	[M+H-H2O]+	147.5	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.8	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	150.9	32859911
AllCCS	[M+HCOO]-	151.2	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indoximod,1TMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2141.0	Semi standard non polar	33892256
Indoximod,1TMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2059.1	Standard non polar	33892256
Indoximod,1TMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2884.7	Standard polar	33892256
Indoximod,1TMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C)C(=O)O)C2=CC=CC=C21	2191.3	Semi standard non polar	33892256
Indoximod,1TMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C)C(=O)O)C2=CC=CC=C21	2080.3	Standard non polar	33892256
Indoximod,1TMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C)C(=O)O)C2=CC=CC=C21	2919.4	Standard polar	33892256
Indoximod,2TMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2127.6	Semi standard non polar	33892256
Indoximod,2TMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2130.1	Standard non polar	33892256
Indoximod,2TMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=CC=CC=C21	2517.3	Standard polar	33892256
Indoximod,2TMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2371.2	Semi standard non polar	33892256
Indoximod,2TMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2250.1	Standard non polar	33892256
Indoximod,2TMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2728.8	Standard polar	33892256
Indoximod,3TMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2358.0	Semi standard non polar	33892256
Indoximod,3TMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2282.4	Standard non polar	33892256
Indoximod,3TMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2458.7	Standard polar	33892256
Indoximod,1TBDMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2403.1	Semi standard non polar	33892256
Indoximod,1TBDMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2263.9	Standard non polar	33892256
Indoximod,1TBDMS,isomer #1	CN1C=C(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2952.8	Standard polar	33892256
Indoximod,1TBDMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C2=CC=CC=C21	2427.9	Semi standard non polar	33892256
Indoximod,1TBDMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C2=CC=CC=C21	2300.9	Standard non polar	33892256
Indoximod,1TBDMS,isomer #2	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C2=CC=CC=C21	2971.5	Standard polar	33892256
Indoximod,2TBDMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2590.7	Semi standard non polar	33892256
Indoximod,2TBDMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2569.4	Standard non polar	33892256
Indoximod,2TBDMS,isomer #1	CN1C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2744.9	Standard polar	33892256
Indoximod,2TBDMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2818.3	Semi standard non polar	33892256
Indoximod,2TBDMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2662.2	Standard non polar	33892256
Indoximod,2TBDMS,isomer #2	CN1C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2846.3	Standard polar	33892256
Indoximod,3TBDMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3003.9	Semi standard non polar	33892256
Indoximod,3TBDMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2903.6	Standard non polar	33892256
Indoximod,3TBDMS,isomer #1	CN1C=C(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2756.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indoximod GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-4920000000-21fcc661678a4db4431b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoximod GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indoximod 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 - Indoximod 10V, Positive-QTOF	splash10-0uxr-0390000000-274888ef32dc3dcdea58	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoximod 20V, Positive-QTOF	splash10-106r-0940000000-cb433965df20265c3092	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoximod 40V, Positive-QTOF	splash10-053r-0900000000-a22e7dda2f18b8bc933e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoximod 10V, Negative-QTOF	splash10-0159-0890000000-3aa75ff4c836f366464a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoximod 20V, Negative-QTOF	splash10-001i-0900000000-6f3ee29445c95dffe439	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indoximod 40V, Negative-QTOF	splash10-004i-0900000000-aca544ad4a2b0c289155	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

88584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1-Methyltryptophan

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

72821

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 Indoximod (HMDB0243932)

MOL for HMDB0243932 (Indoximod)

3D MOL for HMDB0243932 (Indoximod)

3D SDF for HMDB0243932 (Indoximod)

3D-SDF for HMDB0243932 (Indoximod)

PDB for HMDB0243932 (Indoximod)

3D PDB for HMDB0243932 (Indoximod)

SMILES for HMDB0243932 (Indoximod)

INCHI for HMDB0243932 (Indoximod)

Structure for HMDB0243932 (Indoximod)

3D Structure for HMDB0243932 (Indoximod)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra