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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:36:23 UTC

Update Date

2021-09-26 23:03:10 UTC

HMDB ID

HMDB0251272

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Diftalone

Description

5,7,12,14-tetrahydro-6,13-diazatetracene-5,12-dione belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. Based on a literature review a significant number of articles have been published on 5,7,12,14-tetrahydro-6,13-diazatetracene-5,12-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Diftalone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diftalone 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

HMDB0251272
     RDKit          3D
Diftalone
 32 35  0  0  0  0  0  0  0  0999 V2000
   -1.4083    2.5240    0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    1.3038    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.5486    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911    1.1073    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513    0.3862    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8275   -0.9468   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.5043   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4141   -0.7844   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -1.4773   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -0.6478   -0.1516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -1.2994   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379   -2.5195   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5363   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -1.1418   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997   -0.4162   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522    0.9201    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.5156    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.7986    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607    1.5294    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213    0.7082    0.1847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    2.1583    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9340    0.8510    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.5178   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -2.5663   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546   -2.3306    0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019   -1.9230   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -2.1863   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -0.8684   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7849    1.4854    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481    2.5462    0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    2.4087   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.8747    1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  8  3  1  0
 20 10  1  0
 18 13  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 19 32  1  0
M  END


  Mrv1572004221603022D          

 20 23  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   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
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    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
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251272

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1N2CC3=CC=CC=C3C(=O)N2CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O2/c19-15-13-7-3-1-5-11(13)9-17-16(20)14-8-4-2-6-12(14)10-18(15)17/h1-8H,9-10H2

> <INCHI_KEY>
CXSJGNHRBWJXEA-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O2

> <MOLECULAR_WEIGHT>
264.284

> <EXACT_MASS>
264.089877634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.80729714000667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,12,14-tetrahydro-6,13-diazatetracene-5,12-dione

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
2.038417914

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.276790079205196

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
75.5754

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diftalone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251272
     RDKit          3D
Diftalone
 32 35  0  0  0  0  0  0  0  0999 V2000
   -1.4083    2.5240    0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    1.3038    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.5486    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911    1.1073    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513    0.3862    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8275   -0.9468   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.5043   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4141   -0.7844   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -1.4773   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -0.6478   -0.1516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -1.2994   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379   -2.5195   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5363   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -1.1418   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997   -0.4162   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522    0.9201    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.5156    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.7986    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607    1.5294    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213    0.7082    0.1847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    2.1583    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9340    0.8510    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.5178   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -2.5663   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546   -2.3306    0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019   -1.9230   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -2.1863   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -0.8684   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7849    1.4854    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481    2.5462    0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    2.4087   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.8747    1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  8  3  1  0
 20 10  1  0
 18 13  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   14                                                       
CONECT    9   11   17                                                       
CONECT   10   12   18                                                       
CONECT   11    5    9   13                                                  
CONECT   12    6   10   14                                                  
CONECT   13    7   11   15                                                  
CONECT   14    8   12   16                                                  
CONECT   15   13   18   19                                                  
CONECT   16   14   17   20                                                  
CONECT   17    9   16   18                                                  
CONECT   18   10   15   17                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0251272
HETATM    1  O1  UNL     1      -1.408   2.524   0.636  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.312   1.304   0.333  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.523   0.549   0.146  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.791   1.107   0.285  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.951   0.386   0.107  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.827  -0.947  -0.224  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.574  -1.504  -0.362  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.414  -0.784  -0.184  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.134  -1.477  -0.357  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.020  -0.648  -0.152  1.00  0.00           N  
HETATM   11  C9  UNL     1       1.289  -1.299  -0.314  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.338  -2.520  -0.616  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.511  -0.536  -0.125  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.744  -1.142  -0.276  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.900  -0.416  -0.096  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.852   0.920   0.235  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.625   1.516   0.383  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.433   0.799   0.206  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.161   1.529   0.388  1.00  0.00           C  
HETATM   20  N2  UNL     1      -0.021   0.708   0.185  1.00  0.00           N  
HETATM   21  H1  UNL     1      -3.856   2.158   0.546  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.934   0.851   0.223  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.735  -1.518  -0.365  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.544  -2.566  -0.626  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.055  -2.331   0.363  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.102  -1.923  -1.363  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.801  -2.186  -0.535  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.873  -0.868  -0.209  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.785   1.485   0.375  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.548   2.546   0.639  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.187   2.409  -0.277  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.117   1.875   1.448  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    4    8
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9
CONECT    9   10   25   26
CONECT   10   11   20
CONECT   11   12   12   13
CONECT   13   14   14   18
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   20   31   32
END

HMDB0251272
     RDKit          3D
Diftalone
 32 35  0  0  0  0  0  0  0  0999 V2000
   -1.4083    2.5240    0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3124    1.3038    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.5486    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911    1.1073    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513    0.3862    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8275   -0.9468   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.5043   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4141   -0.7844   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -1.4773   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -0.6478   -0.1516 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -1.2994   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379   -2.5195   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.5363   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -1.1418   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997   -0.4162   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522    0.9201    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247    1.5156    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.7986    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607    1.5294    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213    0.7082    0.1847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8559    2.1583    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9340    0.8510    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.5178   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -2.5663   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546   -2.3306    0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019   -1.9230   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -2.1863   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -0.8684   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7849    1.4854    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481    2.5462    0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    2.4087   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.8747    1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  8  3  1  0
 20 10  1  0
 18 13  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-5418DIftalone	ChEMBL
Aladione	MeSH
Diftalone	MeSH
phthalazino-(2,3-b)-Phthalazine-5,12(7H,14H)-dione	MeSH

Chemical Formula

C₁₆H₁₂N₂O₂

Average Molecular Weight

264.284

Monoisotopic Molecular Weight

264.089877634

IUPAC Name

5,7,12,14-tetrahydro-6,13-diazatetracene-5,12-dione

Traditional Name

diftalone

CAS Registry Number

Not Available

SMILES

O=C1N2CC3=CC=CC=C3C(=O)N2CC2=CC=CC=C12

InChI Identifier

InChI=1S/C16H12N2O2/c19-15-13-7-3-1-5-11(13)9-17-16(20)14-8-4-2-6-12(14)10-18(15)17/h1-8H,9-10H2

InChI Key

CXSJGNHRBWJXEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
Phthalazinone
Diazanaphthalene
Phthalazine
Carboxylic acid hydrazide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen 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	1.33	ALOGPS
logP	2.04	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.58 m³·mol⁻¹	ChemAxon
Polarizability	27.81 Å³	ChemAxon
Number of Rings	4	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]-	193.58	30932474
DeepCCS	[M+Na]+	169.145	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diftalone	O=C1N2CC3=CC=CC=C3C(=O)N2CC2=CC=CC=C12	3858.4	Standard polar	33892256
Diftalone	O=C1N2CC3=CC=CC=C3C(=O)N2CC2=CC=CC=C12	2518.6	Standard non polar	33892256
Diftalone	O=C1N2CC3=CC=CC=C3C(=O)N2CC2=CC=CC=C12	2812.9	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 - Diftalone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-3920000000-a392b7a8db075125e06b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diftalone 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 - Diftalone 10V, Positive-QTOF	splash10-014i-0090000000-09d04b94675ed27bfc91	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 20V, Positive-QTOF	splash10-014i-0090000000-bc98343f495561dd1af0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 40V, Positive-QTOF	splash10-014i-5390000000-6a446e6c2d9cfc99a344	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 10V, Negative-QTOF	splash10-03di-0090000000-f2924a9c11c80a277297	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 20V, Negative-QTOF	splash10-03di-0290000000-00a2541f3c39b2281c8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 40V, Negative-QTOF	splash10-03di-0690000000-61c0a27d5ce21ad91243	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 10V, Positive-QTOF	splash10-014i-0090000000-e6e22b9224f216c1ee62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 20V, Positive-QTOF	splash10-014i-0090000000-e6e22b9224f216c1ee62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 40V, Positive-QTOF	splash10-014u-5980000000-de9a00d8e38e10c52829	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 10V, Negative-QTOF	splash10-03di-0090000000-b99e2c8e0534785a5ddc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 20V, Negative-QTOF	splash10-03di-0090000000-b99e2c8e0534785a5ddc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diftalone 40V, Negative-QTOF	splash10-01ot-1790000000-dfa16aa77db4790aa2ef	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

28502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

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 Diftalone (HMDB0251272)

MOL for HMDB0251272 (Diftalone)

3D MOL for HMDB0251272 (Diftalone)

3D SDF for HMDB0251272 (Diftalone)

3D-SDF for HMDB0251272 (Diftalone)

PDB for HMDB0251272 (Diftalone)

3D PDB for HMDB0251272 (Diftalone)

SMILES for HMDB0251272 (Diftalone)

INCHI for HMDB0251272 (Diftalone)

Structure for HMDB0251272 (Diftalone)

3D Structure for HMDB0251272 (Diftalone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra