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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:12:28 UTC

Update Date

2021-09-26 23:08:59 UTC

HMDB ID

HMDB0254762

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mitonafide

Description

Mitonafide belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro groups. Based on a literature review a significant number of articles have been published on Mitonafide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mitonafide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mitonafide 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

HMDB0254762
     RDKit          3D
Mitonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.9801    0.3711    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2047    0.7286   -0.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.0021   -1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    0.8400   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -0.4653   -0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264   -0.3369    0.0241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -0.1182    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226   -0.0409    2.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    0.0274    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.2387    2.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.3701    3.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    0.2904    2.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345    0.0790    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880    0.0036   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166   -0.2073   -1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.2799   -2.4039 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7142   -0.4614   -3.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293   -0.1452   -2.0642 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6699   -0.3365   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.2628   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -0.0503    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858   -0.4067   -0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -0.5970   -2.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2662    1.3518    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -0.3286    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490   -0.0735    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7015   -0.1733   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    0.6436   -2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -0.9721   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    1.3401   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    1.4626    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.9064    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328   -1.1476   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.2993    3.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    0.5344    4.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.3887    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4449    0.1138    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.5050   -2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 22  6  1  0
 21  9  2  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
M  CHG  2  16   1  18  -1
M  END


  Mrv1652309112116122D          

 23 25  0  0  0  0            999 V2000
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  9 18  1  0  0  0  0
 17 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  CHG  2  21   1  23  -1
M  END
> <DATABASE_ID>
HMDB0254762

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H15N3O4/c1-17(2)6-7-18-15(20)12-5-3-4-10-8-11(19(22)23)9-13(14(10)12)16(18)21/h3-5,8-9H,6-7H2,1-2H3

> <INCHI_KEY>
XXVLKDRPHSFIIB-UHFFFAOYSA-N

> <FORMULA>
C16H15N3O4

> <MOLECULAR_WEIGHT>
313.313

> <EXACT_MASS>
313.106255975

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.58647291565717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-11-nitro-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.8652045723333335

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.517467340142947

> <JCHEM_POLAR_SURFACE_AREA>
83.76

> <JCHEM_REFRACTIVITY>
85.00129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(dimethylamino)ethyl]-11-nitro-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254762
     RDKit          3D
Mitonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.9801    0.3711    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2047    0.7286   -0.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.0021   -1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    0.8400   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -0.4653   -0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264   -0.3369    0.0241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -0.1182    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226   -0.0409    2.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    0.0274    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.2387    2.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.3701    3.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    0.2904    2.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345    0.0790    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880    0.0036   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166   -0.2073   -1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.2799   -2.4039 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7142   -0.4614   -3.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293   -0.1452   -2.0642 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6699   -0.3365   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.2628   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -0.0503    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858   -0.4067   -0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -0.5970   -2.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2662    1.3518    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -0.3286    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490   -0.0735    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7015   -0.1733   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    0.6436   -2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -0.9721   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    1.3401   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    1.4626    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.9064    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328   -1.1476   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.2993    3.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    0.5344    4.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.3887    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4449    0.1138    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.5050   -2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 22  6  1  0
 21  9  2  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
M  CHG  2  16   1  18  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   13    9                                                  
CONECT   19   17    6   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0254762
HETATM    1  C1  UNL     1      -4.980   0.371   0.452  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.205   0.729  -0.712  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.595   0.002  -1.889  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.808   0.840  -0.495  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.128  -0.465  -0.207  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.726  -0.337   0.024  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.292  -0.118   1.359  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.123  -0.041   2.310  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.134   0.027   1.690  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.552   0.239   2.985  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.891   0.370   3.266  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.813   0.290   2.254  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.434   0.079   0.936  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.388   0.004  -0.070  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.017  -0.207  -1.383  1.00  0.00           C  
HETATM   16  N3  UNL     1       5.003  -0.280  -2.404  1.00  0.00           N1+
HETATM   17  O2  UNL     1       4.714  -0.461  -3.601  1.00  0.00           O  
HETATM   18  O3  UNL     1       6.329  -0.145  -2.064  1.00  0.00           O1-
HETATM   19  C13 UNL     1       2.670  -0.337  -1.637  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.718  -0.263  -0.645  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.078  -0.050   0.680  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.286  -0.407  -0.962  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.055  -0.597  -2.140  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.266   1.352   0.938  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.504  -0.329   1.137  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.949  -0.073   0.138  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.702  -0.173  -1.840  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.458   0.644  -2.784  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.107  -0.972  -2.016  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.339   1.340  -1.359  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.688   1.463   0.443  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.596  -0.906   0.696  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.233  -1.148  -1.098  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.821   0.299   3.773  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.232   0.534   4.271  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.878   0.389   2.431  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.445   0.114   0.190  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.350  -0.505  -2.668  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    9   10   21   21
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   21
CONECT   14   15   15   37
CONECT   15   16   19
CONECT   16   17   17   18
CONECT   19   20   20   38
CONECT   20   21   22
CONECT   22   23   23
END

HMDB0254762
     RDKit          3D
Mitonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.9801    0.3711    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2047    0.7286   -0.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.0021   -1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    0.8400   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -0.4653   -0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264   -0.3369    0.0241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2918   -0.1182    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226   -0.0409    2.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    0.0274    1.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.2387    2.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.3701    3.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    0.2904    2.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345    0.0790    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880    0.0036   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166   -0.2073   -1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034   -0.2799   -2.4039 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7142   -0.4614   -3.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293   -0.1452   -2.0642 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6699   -0.3365   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.2628   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0777   -0.0503    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858   -0.4067   -0.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -0.5970   -2.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2662    1.3518    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -0.3286    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9490   -0.0735    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7015   -0.1733   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    0.6436   -2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -0.9721   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    1.3401   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    1.4626    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.9064    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328   -1.1476   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.2993    3.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    0.5344    4.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.3887    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4449    0.1138    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.5050   -2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 22  6  1  0
 21  9  2  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
M  CHG  2  16   1  18  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(2-(Dimethylamino)ethyl)-5-nitro-1H-benz(de)isoquinoline-1,3(2H)-dione	MeSH
2-Dimethylaminoethylbenzo(de)isoquinoline-1,3-dione hydrochloride	MeSH
5-Nitro-2-(2-dimethylaminoethyl)benzo(de)isoquinoline-1,3-dione	MeSH
N-(2-Dimethylaminoethyl)-3-nitro-naphthalimide	MeSH
N-(2-Dimethylaminoethyl)-3-nitronaphthalimide	MeSH

Chemical Formula

C₁₆H₁₅N₃O₄

Average Molecular Weight

313.313

Monoisotopic Molecular Weight

313.106255975

IUPAC Name

3-[2-(dimethylamino)ethyl]-11-nitro-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione

Traditional Name

3-[2-(dimethylamino)ethyl]-11-nitro-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione

CAS Registry Number

Not Available

SMILES

CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O

InChI Identifier

InChI=1S/C16H15N3O4/c1-17(2)6-7-18-15(20)12-5-3-4-10-8-11(19(22)23)9-13(14(10)12)16(18)21/h3-5,8-9H,6-7H2,1-2H3

InChI Key

XXVLKDRPHSFIIB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-nitronaphthalene
Isoquinolone
Nitroaromatic compound
Carboxylic acid imide, n-substituted
Carboxylic acid imide
Amino acid or derivatives
C-nitro compound
Tertiary amine
Tertiary aliphatic amine
Organic nitro compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic oxoazanium
Organic nitrogen compound
Organic salt
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organic oxygen compound
Organooxygen compound
Organic cation
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	1.68	ALOGPS
logP	1.87	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	8.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85 m³·mol⁻¹	ChemAxon
Polarizability	31.59 Å³	ChemAxon
Number of Rings	3	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]-	207.222	30932474
DeepCCS	[M+Na]+	183.387	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.2	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	174.3	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mitonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O	4196.8	Standard polar	33892256
Mitonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O	2682.6	Standard non polar	33892256
Mitonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O	2806.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mitonafide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9050000000-26b31d7d68feba1a4cda	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mitonafide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

289622

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

327044

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 Mitonafide (HMDB0254762)

MOL for HMDB0254762 (Mitonafide)

3D MOL for HMDB0254762 (Mitonafide)

3D SDF for HMDB0254762 (Mitonafide)

3D-SDF for HMDB0254762 (Mitonafide)

PDB for HMDB0254762 (Mitonafide)

3D PDB for HMDB0254762 (Mitonafide)

SMILES for HMDB0254762 (Mitonafide)

INCHI for HMDB0254762 (Mitonafide)

Structure for HMDB0254762 (Mitonafide)

3D Structure for HMDB0254762 (Mitonafide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra