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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:23:07 UTC

Update Date

2021-09-26 23:09:19 UTC

HMDB ID

HMDB0254904

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Motolimod

Description

Motolimod belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom). Motolimod is a very strong basic compound (based on its pKa). In June 2018, the combination of BRAFTOVI® (encorafenib) and MEKTOVI® (binimetinib) was approved by the Food and Drug Administration for the treatment of people with unresectable or metastatic BRAF V600E or V600K mutation-positive melanoma. In 2017, the company spun out one of its programs into a subsidiary called Yarra; the asset was a molecule called ARRY-797 that was in a Phase II trial for cardiomyopathy. In May 2017, the company partnered with Ono Pharmaceutical to test the combination of binimetinib and encorafenib while retaining commercialization rights in the U.S. and other markets. In July 2019, Pfizer acquired the company. In November 2015, the company signed a partnership with Laboratoires Pierre Fabre. The company focuses on oncology medication. Array BioPharma is a U.S.-based, clinical stage, pharmaceutical company. In July 2013, the company partnered with Loxo Oncology to develop cancer drugs. This compound has been identified in human blood as reported by (PMID: 31557052 ). Motolimod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Motolimod 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


  Mrv1652310201623522D          

 34 37  0  0  0  0            999 V2000
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M  END

HMDB0254904
     RDKit          3D
Motolimod
 68 71  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652310201623522D          

 34 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0254904

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN(CCC)C(=O)C1=CC2=CC=C(C=C2N=C(N)C1)C1=CC=C(C=C1)C(=O)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34N4O2/c1-3-13-31(14-4-2)28(34)24-17-23-12-11-22(18-25(23)30-26(29)19-24)20-7-9-21(10-8-20)27(33)32-15-5-6-16-32/h7-12,17-18H,3-6,13-16,19H2,1-2H3,(H2,29,30)

> <INCHI_KEY>
QSPOQCXMGPDIHI-UHFFFAOYSA-N

> <FORMULA>
C28H34N4O2

> <MOLECULAR_WEIGHT>
458.606

> <EXACT_MASS>
458.268176351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.06193485296104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
3.744785925666667

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.925190489208614

> <JCHEM_POLAR_SURFACE_AREA>
78.99999999999999

> <JCHEM_REFRACTIVITY>
140.02509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254904
     RDKit          3D
Motolimod
 68 71  0  0  0  0  0  0  0  0999 V2000
   -7.5028    2.7755    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4487    2.5453   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3898    1.1376   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    0.1399    0.3575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2665   -0.4852    1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8067   -1.6436    0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -2.7932    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8431   -0.3134    0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.2396    1.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -0.0062    0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -0.7280    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -0.6542    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -0.9977    1.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -0.9802    1.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -0.6299    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -0.6077    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9043   -1.4916    1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2722   -1.5273    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0331   -0.6401    0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4728   -0.7223    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.5152    1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3883   -0.0248   -0.0895 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8531   -0.1716    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3884   -0.0664   -1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5336    1.0164   -1.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1982    0.8735   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2884    0.2322   -0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824    0.2647   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -0.2848   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3871   -0.2984   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312    0.0510   -1.5706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    0.6102   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    0.8616   -3.0565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    1.0352   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1820    2.3136    1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5529    3.8951    1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5252    2.5211    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5557    3.2876   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4715    2.8100    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4889    0.9571   -0.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8593    1.0502   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029   -0.8337    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0872    0.2441    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6415   -2.0686    0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3237   -1.3614   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3295   -3.5678   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5779   -3.2766    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9221   -2.5264   -0.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904   -1.4244    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -1.2674    2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -1.2493    2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706   -2.1958    2.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8447   -2.2262    2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2160    0.6370    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0390   -1.1809    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4655    0.1923   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2672   -0.9990   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9809    2.0088   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4107    0.9281   -2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8425    1.8759   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038    0.4415   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7810    0.9490   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    0.9798   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721    0.0006   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279    0.4429   -3.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    1.4638   -3.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.7191   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347    1.7386    0.0003 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  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  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 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  2  0
 15 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 10  1  0
 30 12  1  0
 28 16  1  0
 26 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  7 48  1  0
 11 49  1  0
 13 50  1  0
 14 51  1  0
 17 52  1  0
 18 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 28 63  1  0
 29 64  1  0
 33 65  1  0
 33 66  1  0
 34 67  1  0
 34 68  1  0
M  END

HEADER    PROTEIN                                 20-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-OCT-16         0                                  
HETATM    1  C   UNK     0       1.236  -6.058   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.776  -6.058   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.546  -4.724   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.086  -4.724   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.856  -6.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.396  -6.058   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.166  -7.392   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.856  -3.391   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.086  -2.057   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.396  -3.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.065  -2.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.566  -1.660   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.796  -0.138   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.229   0.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.433  -0.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.204  -2.058   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.770  -2.621   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.770  -4.161   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       9.566  -5.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.065  -4.778   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.909  -6.622   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      13.867   0.028   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.096   1.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.530   2.113   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.734   1.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.504  -0.370   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.071  -0.933   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.167   1.715   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.397   3.238   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0      19.371   0.755   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      20.856   1.165   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.704  -0.120   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.744  -1.324   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.302  -0.783   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   10                                                       
CONECT   21   19                                                            
CONECT   22   15   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0254904
HETATM    1  C1  UNL     1      -7.503   2.776   0.944  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.449   2.545  -0.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.390   1.138  -0.624  1.00  0.00           C  
HETATM    4  N1  UNL     1      -6.090   0.140   0.357  1.00  0.00           N  
HETATM    5  C4  UNL     1      -7.267  -0.485   1.000  1.00  0.00           C  
HETATM    6  C5  UNL     1      -7.807  -1.644   0.249  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.855  -2.793   0.040  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.843  -0.313   0.740  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.911  -1.240   1.682  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.495  -0.006   0.344  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.528  -0.728   0.979  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.070  -0.654   0.795  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.359  -0.998   1.920  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.028  -0.980   1.881  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.722  -0.630   0.753  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.174  -0.608   0.694  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.904  -1.492   1.444  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.272  -1.527   1.435  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.033  -0.640   0.638  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.473  -0.722   0.705  1.00  0.00           C  
HETATM   21  O2  UNL     1       8.002  -1.515   1.579  1.00  0.00           O  
HETATM   22  N2  UNL     1       8.388  -0.025  -0.090  1.00  0.00           N  
HETATM   23  C19 UNL     1       9.853  -0.172   0.107  1.00  0.00           C  
HETATM   24  C20 UNL     1      10.388  -0.066  -1.287  1.00  0.00           C  
HETATM   25  C21 UNL     1       9.534   1.016  -1.897  1.00  0.00           C  
HETATM   26  C22 UNL     1       8.198   0.873  -1.176  1.00  0.00           C  
HETATM   27  C23 UNL     1       5.288   0.232  -0.100  1.00  0.00           C  
HETATM   28  C24 UNL     1       3.882   0.265  -0.087  1.00  0.00           C  
HETATM   29  C25 UNL     1       0.977  -0.285  -0.378  1.00  0.00           C  
HETATM   30  C26 UNL     1      -0.387  -0.298  -0.353  1.00  0.00           C  
HETATM   31  N3  UNL     1      -1.031   0.051  -1.571  1.00  0.00           N  
HETATM   32  C27 UNL     1      -2.212   0.610  -1.714  1.00  0.00           C  
HETATM   33  N4  UNL     1      -2.645   0.862  -3.057  1.00  0.00           N  
HETATM   34  C28 UNL     1      -3.127   1.035  -0.629  1.00  0.00           C  
HETATM   35  H1  UNL     1      -7.182   2.314   1.882  1.00  0.00           H  
HETATM   36  H2  UNL     1      -7.553   3.895   1.118  1.00  0.00           H  
HETATM   37  H3  UNL     1      -8.525   2.521   0.609  1.00  0.00           H  
HETATM   38  H4  UNL     1      -6.556   3.288  -0.925  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.472   2.810   0.392  1.00  0.00           H  
HETATM   40  H6  UNL     1      -7.489   0.957  -0.998  1.00  0.00           H  
HETATM   41  H7  UNL     1      -5.859   1.050  -1.586  1.00  0.00           H  
HETATM   42  H8  UNL     1      -7.003  -0.834   2.028  1.00  0.00           H  
HETATM   43  H9  UNL     1      -8.087   0.244   1.131  1.00  0.00           H  
HETATM   44  H10 UNL     1      -8.641  -2.069   0.883  1.00  0.00           H  
HETATM   45  H11 UNL     1      -8.324  -1.361  -0.698  1.00  0.00           H  
HETATM   46  H12 UNL     1      -7.329  -3.568  -0.643  1.00  0.00           H  
HETATM   47  H13 UNL     1      -6.578  -3.277   0.999  1.00  0.00           H  
HETATM   48  H14 UNL     1      -5.922  -2.526  -0.481  1.00  0.00           H  
HETATM   49  H15 UNL     1      -2.890  -1.424   1.713  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.929  -1.267   2.781  1.00  0.00           H  
HETATM   51  H17 UNL     1       1.591  -1.249   2.762  1.00  0.00           H  
HETATM   52  H18 UNL     1       3.371  -2.196   2.075  1.00  0.00           H  
HETATM   53  H19 UNL     1       5.845  -2.226   2.026  1.00  0.00           H  
HETATM   54  H20 UNL     1      10.216   0.637   0.766  1.00  0.00           H  
HETATM   55  H21 UNL     1      10.039  -1.181   0.465  1.00  0.00           H  
HETATM   56  H22 UNL     1      11.466   0.192  -1.286  1.00  0.00           H  
HETATM   57  H23 UNL     1      10.267  -0.999  -1.852  1.00  0.00           H  
HETATM   58  H24 UNL     1       9.981   2.009  -1.701  1.00  0.00           H  
HETATM   59  H25 UNL     1       9.411   0.928  -2.990  1.00  0.00           H  
HETATM   60  H26 UNL     1       7.842   1.876  -0.863  1.00  0.00           H  
HETATM   61  H27 UNL     1       7.504   0.441  -1.961  1.00  0.00           H  
HETATM   62  H28 UNL     1       5.781   0.949  -0.714  1.00  0.00           H  
HETATM   63  H29 UNL     1       3.358   0.980  -0.696  1.00  0.00           H  
HETATM   64  H30 UNL     1       1.472   0.001  -1.298  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.528   0.443  -3.414  1.00  0.00           H  
HETATM   66  H32 UNL     1      -2.099   1.464  -3.711  1.00  0.00           H  
HETATM   67  H33 UNL     1      -3.891   1.719  -0.956  1.00  0.00           H  
HETATM   68  H34 UNL     1      -2.435   1.739   0.000  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5    8
CONECT    5    6   42   43
CONECT    6    7   44   45
CONECT    7   46   47   48
CONECT    8    9    9   10
CONECT   10   11   11   34
CONECT   11   12   49
CONECT   12   13   13   30
CONECT   13   14   50
CONECT   14   15   15   51
CONECT   15   16   29
CONECT   16   17   17   28
CONECT   17   18   52
CONECT   18   19   19   53
CONECT   19   20   27
CONECT   20   21   21   22
CONECT   22   23   26
CONECT   23   24   54   55
CONECT   24   25   56   57
CONECT   25   26   58   59
CONECT   26   60   61
CONECT   27   28   28   62
CONECT   28   63
CONECT   29   30   30   64
CONECT   30   31
CONECT   31   32   32
CONECT   32   33   34
CONECT   33   65   66
CONECT   34   67   68
END

HMDB0254904
     RDKit          3D
Motolimod
 68 71  0  0  0  0  0  0  0  0999 V2000
   -7.5028    2.7755    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4487    2.5453   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3898    1.1376   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    0.1399    0.3575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2665   -0.4852    1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8067   -1.6436    0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -2.7932    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8431   -0.3134    0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.2396    1.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -0.0062    0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -0.7280    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -0.6542    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -0.9977    1.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -0.9802    1.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -0.6299    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -0.6077    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9043   -1.4916    1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2722   -1.5273    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0331   -0.6401    0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4728   -0.7223    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.5152    1.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3883   -0.0248   -0.0895 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8531   -0.1716    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3884   -0.0664   -1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5336    1.0164   -1.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1982    0.8735   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2884    0.2322   -0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824    0.2647   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -0.2848   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3871   -0.2984   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312    0.0510   -1.5706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    0.6102   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    0.8616   -3.0565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272    1.0352   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1820    2.3136    1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5529    3.8951    1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5252    2.5211    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5557    3.2876   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4715    2.8100    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4889    0.9571   -0.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8593    1.0502   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029   -0.8337    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0872    0.2441    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6415   -2.0686    0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3237   -1.3614   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3295   -3.5678   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5779   -3.2766    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9221   -2.5264   -0.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904   -1.4244    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -1.2674    2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -1.2493    2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706   -2.1958    2.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8447   -2.2262    2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2160    0.6370    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0390   -1.1809    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4655    0.1923   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2672   -0.9990   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9809    2.0088   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4107    0.9281   -2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8425    1.8759   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038    0.4415   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7810    0.9490   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    0.9798   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721    0.0006   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279    0.4429   -3.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989    1.4638   -3.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.7191   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347    1.7386    0.0003 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  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  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 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  2  0
 15 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 10  1  0
 30 12  1  0
 28 16  1  0
 26 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  7 48  1  0
 11 49  1  0
 13 50  1  0
 14 51  1  0
 17 52  1  0
 18 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 28 63  1  0
 29 64  1  0
 33 65  1  0
 33 66  1  0
 34 67  1  0
 34 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
VTX-378VTX-2337MOTOLIMOD	ChEMBL

Chemical Formula

C₂₈H₃₄N₄O₂

Average Molecular Weight

458.606

Monoisotopic Molecular Weight

458.268176351

IUPAC Name

2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide

Traditional Name

2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide

CAS Registry Number

Not Available

SMILES

CCCN(CCC)C(=O)C1=CC2=CC=C(C=C2N=C(N)C1)C1=CC=C(C=C1)C(=O)N1CCCC1

InChI Identifier

InChI=1S/C28H34N4O2/c1-3-13-31(14-4-2)28(34)24-17-23-12-11-22(18-25(23)30-26(29)19-24)20-7-9-21(10-8-20)27(33)32-15-5-6-16-32/h7-12,17-18H,3-6,13-16,19H2,1-2H3,(H2,29,30)

InChI Key

QSPOQCXMGPDIHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Benzamide
Benzoic acid or derivatives
Benzoyl
N-acylpyrrolidine
Azepine
Monocyclic benzene moiety
Imidolactam
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Amidine
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
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)

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	4.67	ALOGPS
logP	3.74	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.03 m³·mol⁻¹	ChemAxon
Polarizability	54.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	219.734	30932474
DeepCCS	[M-H]-	217.338	30932474
DeepCCS	[M-2H]-	250.221	30932474
DeepCCS	[M+Na]+	225.646	30932474
AllCCS	[M+H]+	213.6	32859911
AllCCS	[M+H-H2O]+	211.5	32859911
AllCCS	[M+NH4]+	215.5	32859911
AllCCS	[M+Na]+	216.1	32859911
AllCCS	[M-H]-	209.6	32859911
AllCCS	[M+Na-2H]-	211.3	32859911
AllCCS	[M+HCOO]-	213.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Motolimod	CCCN(CCC)C(=O)C1=CC2=CC=C(C=C2N=C(N)C1)C1=CC=C(C=C1)C(=O)N1CCCC1	5348.8	Standard polar	33892256
Motolimod	CCCN(CCC)C(=O)C1=CC2=CC=C(C=C2N=C(N)C1)C1=CC=C(C=C1)C(=O)N1CCCC1	4365.7	Standard non polar	33892256
Motolimod	CCCN(CCC)C(=O)C1=CC2=CC=C(C=C2N=C(N)C1)C1=CC=C(C=C1)C(=O)N1CCCC1	4486.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Motolimod,1TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C)C1	4295.4	Semi standard non polar	33892256
Motolimod,1TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C)C1	3865.8	Standard non polar	33892256
Motolimod,1TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C)C1	5902.2	Standard polar	33892256
Motolimod,2TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)C1	4334.1	Semi standard non polar	33892256
Motolimod,2TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)C1	3985.6	Standard non polar	33892256
Motolimod,2TMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)C1	5647.5	Standard polar	33892256
Motolimod,1TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C(C)(C)C)C1	4518.7	Semi standard non polar	33892256
Motolimod,1TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C(C)(C)C)C1	4073.3	Standard non polar	33892256
Motolimod,1TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N[Si](C)(C)C(C)(C)C)C1	5853.6	Standard polar	33892256
Motolimod,2TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	4689.7	Semi standard non polar	33892256
Motolimod,2TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	4384.3	Standard non polar	33892256
Motolimod,2TBDMS,isomer #1	CCCN(CCC)C(=O)C1=CC2=CC=C(C3=CC=C(C(=O)N4CCCC4)C=C3)C=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	5581.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Motolimod GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-3009300000-61d176283c6bb192a7bd	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Motolimod 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 - Motolimod 10V, Positive-QTOF	splash10-0a4i-2103900000-96e519c0f62aa7e1d6af	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 20V, Positive-QTOF	splash10-0536-4119400000-185e29e9ad83af1e38e9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 40V, Positive-QTOF	splash10-0006-9060000000-38b8ce6b0bf61ff65a1b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 10V, Negative-QTOF	splash10-0a4i-0000900000-115bd3957f84fd7a694a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 20V, Negative-QTOF	splash10-0a4j-5403900000-ab185407c25bf177ee1e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 40V, Negative-QTOF	splash10-0006-9001000000-1f12a104754b39bd0868	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 10V, Positive-QTOF	splash10-0a4i-0001900000-42b59379cf8899f1475d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 20V, Positive-QTOF	splash10-0a4i-8009700000-5c4cf7cbaf88fa75d85c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 40V, Positive-QTOF	splash10-0006-9015400000-7883eddcffe3c39ceade	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 10V, Negative-QTOF	splash10-0a4i-0000900000-3730f7726aac8ae4ca8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 20V, Negative-QTOF	splash10-0a4i-1103900000-921d0b065b69f91e1f8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Motolimod 40V, Negative-QTOF	splash10-053r-4019300000-295124a047502e5cd1e6	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

DB12303

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Array BioPharma

METLIN ID

Not Available

PubChem Compound

16049404

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 Motolimod (HMDB0254904)

MOL for HMDB0254904 (Motolimod)

3D MOL for HMDB0254904 (Motolimod)

3D SDF for HMDB0254904 (Motolimod)

3D-SDF for HMDB0254904 (Motolimod)

PDB for HMDB0254904 (Motolimod)

3D PDB for HMDB0254904 (Motolimod)

SMILES for HMDB0254904 (Motolimod)

INCHI for HMDB0254904 (Motolimod)

Structure for HMDB0254904 (Motolimod)

3D Structure for HMDB0254904 (Motolimod)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra