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Showing metabocard for 7,7,8,8-Tetracyanoquinodimethane (HMDB0244685)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:49:44 UTC
Update Date2021-09-26 22:52:36 UTC
HMDB IDHMDB0244685
Secondary Accession NumbersNone
Metabolite Identification
Common Name7,7,8,8-Tetracyanoquinodimethane
Description7,7,8,8-Tetracyanoquinodimethane, also known as TCNQ, belongs to the class of organic compounds known as p-quinodimethanes. P-quinodimethanes are compounds containing a benzene ring conjugated to two methylidene groups at carbon atoms 1 and 4, respectively. Based on a literature review a significant number of articles have been published on 7,7,8,8-Tetracyanoquinodimethane. This compound has been identified in human blood as reported by (PMID: 31557052 ). 7,7,8,8-tetracyanoquinodimethane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 7,7,8,8-Tetracyanoquinodimethane 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

  Mrv0541 02241205242D          

 16 16  0  0  0  0            999 V2000
    2.1434   -2.0625    0.0000 N   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    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
    0.7145    2.0625    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
   -0.7145    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
    2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  3  0  0  0  0
  3  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 12 15  1  0  0  0  0
 15 16  3  0  0  0  0
M  END
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3D MOL for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

HMDB0244685
     RDKit          3D
7,7,8,8-Tetracyanoquinodimethane
 20 20  0  0  0  0  0  0  0  0999 V2000
   -4.4324    0.7017    1.1185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412    0.2654    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6450   -0.2721   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1405   -0.9626   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -1.5181   -2.6091 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522   -0.1411   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232   -0.6624   -1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.5381   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.1353    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448    0.2721    0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -0.2567   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.6824   -1.0745 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    0.9694    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3647    1.5326    2.6309 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490    0.6718    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.5143    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032   -1.2035   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.9542   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    1.1861    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100    0.9424    1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  3  0
  3  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  3  0
 10 13  1  0
 13 14  3  0
  9 15  1  0
 15 16  2  0
 16  6  1  0
  7 17  1  0
  8 18  1  0
 15 19  1  0
 16 20  1  0
M  END
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3D SDF for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

  Mrv0541 02241205242D          

 16 16  0  0  0  0            999 V2000
    2.1434   -2.0625    0.0000 N   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    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
    0.7145    2.0625    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
   -0.7145    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
    2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  3  0  0  0  0
  3  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 12 15  1  0  0  0  0
 15 16  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244685

> <DATABASE_NAME>
hmdb

> <SMILES>
N#CC(C#N)=C1C=CC(C=C1)=C(C#N)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H

> <INCHI_KEY>
PCCVSPMFGIFTHU-UHFFFAOYSA-N

> <FORMULA>
C12H4N4

> <MOLECULAR_WEIGHT>
204.187

> <EXACT_MASS>
204.043596148

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.97405559537925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
0.7475403093333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
95.16

> <JCHEM_REFRACTIVITY>
61.188400000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetracyanoquinodimethane

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

HMDB0244685
     RDKit          3D
7,7,8,8-Tetracyanoquinodimethane
 20 20  0  0  0  0  0  0  0  0999 V2000
   -4.4324    0.7017    1.1185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412    0.2654    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6450   -0.2721   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1405   -0.9626   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -1.5181   -2.6091 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522   -0.1411   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232   -0.6624   -1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.5381   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.1353    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448    0.2721    0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -0.2567   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.6824   -1.0745 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    0.9694    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3647    1.5326    2.6309 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490    0.6718    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.5143    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032   -1.2035   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.9542   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    1.1861    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100    0.9424    1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  3  0
  3  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  3  0
 10 13  1  0
 13 14  3  0
  9 15  1  0
 15 16  2  0
 16  6  1  0
  7 17  1  0
  8 18  1  0
 15 19  1  0
 16 20  1  0
M  END
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PDB for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       4.001  -3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.334  -3.850   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   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  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001   5.390   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END
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3D PDB for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

COMPND    HMDB0244685
HETATM    1  N1  UNL     1      -4.432   0.702   1.118  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.641   0.265   0.388  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.645  -0.272  -0.498  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.141  -0.963  -1.664  1.00  0.00           C  
HETATM    5  N2  UNL     1      -3.548  -1.518  -2.609  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.352  -0.141  -0.258  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.423  -0.662  -1.118  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.936  -0.538  -0.889  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.357   0.135   0.247  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.645   0.272   0.497  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.655  -0.257  -0.375  1.00  0.00           C  
HETATM   12  N3  UNL     1       4.473  -0.682  -1.074  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.053   0.969   1.673  1.00  0.00           C  
HETATM   14  N4  UNL     1       3.365   1.533   2.631  1.00  0.00           N  
HETATM   15  C11 UNL     1       0.449   0.672   1.133  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.906   0.514   0.848  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.703  -1.204  -2.030  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.658  -0.954  -1.575  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.811   1.186   2.001  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.610   0.942   1.555  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    6    6
CONECT    4    5    5    5
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   18
CONECT    9   10   10   15
CONECT   10   11   13
CONECT   11   12   12   12
CONECT   13   14   14   14
CONECT   15   16   16   19
CONECT   16   20
END
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SMILES for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

N#CC(C#N)=C1C=CC(C=C1)=C(C#N)C#N
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INCHI for HMDB0244685 (7,7,8,8-Tetracyanoquinodimethane)

InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrileChEBI
2,5-Cyclohexadiene-1,4-diylidenedimalononitrileChEBI
2,5-Cyclohexadiene-delta1,alpha:4,alpha'-dimalononitrileChEBI
7,7',8,8'-TetracyanoquinodimethaneChEBI
7,7,8,8-Tetracyano-1,4-quinodimethanChEBI
7,7,8,8-Tetracyano-p-quinodimethaneChEBI
TCNQChEBI
Tetracyano-p-quinodimethaneChEBI
2,5-Cyclohexadiene-1,4-diylidene-a,alpha'-dimalononitrileGenerator
2,5-Cyclohexadiene-1,4-diylidene-α,alpha'-dimalononitrileGenerator
2,5-Cyclohexadiene-δ1,alpha:4,alpha'-dimalononitrileGenerator
TetracyanoquinonedimethaneHMDB
7,7,8,8-TetracyanoquinodimethaneChEBI
Chemical FormulaC12H4N4
Average Molecular Weight204.187
Monoisotopic Molecular Weight204.043596148
IUPAC Name2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
Traditional Nametetracyanoquinodimethane
CAS Registry NumberNot Available
SMILES
N#CC(C#N)=C1C=CC(C=C1)=C(C#N)C#N
InChI Identifier
InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
InChI KeyPCCVSPMFGIFTHU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-quinodimethanes. P-quinodimethanes are compounds containing a benzene ring conjugated to two methylidene groups at carbon atoms 1 and 4, respectively..
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassQuinodimethanes
Sub ClassP-quinodimethanes
Direct ParentP-quinodimethanes
Alternative Parents
Substituents
  • P-quinodimethane
  • Benzenoid
  • Monocyclic benzene moiety
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.47ALOGPS
logP0.75ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area95.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.19 m³·mol⁻¹ChemAxon
Polarizability19.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID66342
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linktetracyanoquinodimethane
METLIN IDNot Available
PubChem Compound73697
PDB IDNot Available
ChEBI ID52445
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]