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Showing metabocard for 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (HMDB0247511)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:31:00 UTC
Update Date2021-09-26 22:57:15 UTC
HMDB IDHMDB0247511
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Description2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, also known as 2,3-DDQ, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Based on a literature review a significant number of articles have been published on 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 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 HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)


  Mrv1652309112102312D          

 14 14  0  0  0  0            999 V2000
    0.7145    2.0625    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
    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
    2.1434   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  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    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  3  0  0  0  0
M  END
Download

3D MOL for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

HMDB0247511
     RDKit          3D
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.8872    0.9842    1.9207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554    0.7309    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    0.3996    0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -0.8654    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902   -1.8470    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3935   -2.6306    0.7983 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -1.1591   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -2.3533   -0.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787   -0.1669   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203   -0.5526   -1.8816 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3942    1.0794   -0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    2.3385   -0.9774 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2078    1.4211    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666    2.6212    0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  3  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  3  1  0
M  END
Download

3D SDF for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)


  Mrv1652309112102312D          

 14 14  0  0  0  0            999 V2000
    0.7145    2.0625    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
    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
    2.1434   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  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    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247511

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13

> <INCHI_KEY>
HZNVUJQVZSTENZ-UHFFFAOYSA-N

> <FORMULA>
C8Cl2N2O2

> <MOLECULAR_WEIGHT>
227.0

> <EXACT_MASS>
225.9336826

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
17.973803753617112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.425735688

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
81.72

> <JCHEM_REFRACTIVITY>
50.718600000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

HMDB0247511
     RDKit          3D
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.8872    0.9842    1.9207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554    0.7309    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    0.3996    0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -0.8654    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902   -1.8470    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3935   -2.6306    0.7983 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -1.1591   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -2.3533   -0.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787   -0.1669   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203   -0.5526   -1.8816 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3942    1.0794   -0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    2.3385   -0.9774 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2078    1.4211    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666    2.6212    0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  3  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  3  1  0
M  END
Download

PDB for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

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   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.335   3.080   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1    4    9                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    4   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

COMPND    HMDB0247511
HETATM    1  N1  UNL     1      -2.887   0.984   1.921  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.955   0.731   1.299  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.765   0.400   0.533  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.604  -0.865   0.157  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.590  -1.847   0.510  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.394  -2.631   0.798  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.588  -1.159  -0.602  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.762  -2.353  -0.971  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.579  -0.167  -0.957  1.00  0.00           C  
HETATM   10 CL1  UNL     1       3.020  -0.553  -1.882  1.00  0.00          CL  
HETATM   11  C7  UNL     1       1.394   1.079  -0.571  1.00  0.00           C  
HETATM   12 CL2  UNL     1       2.578   2.338  -0.977  1.00  0.00          CL  
HETATM   13  C8  UNL     1       0.208   1.421   0.196  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.067   2.621   0.546  1.00  0.00           O  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5    7
CONECT    5    6    6    6
CONECT    7    8    8    9
CONECT    9   10   11   11
CONECT   11   12   13
CONECT   13   14   14
END
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SMILES for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O
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INCHI for HMDB0247511 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,3-DDQHMDB
2,3-Dichloro-5,6-dicyanobenzoquinoneHMDB
DichlorodicyanobenzoquinoneHMDB
Chemical FormulaC8Cl2N2O2
Average Molecular Weight227.0
Monoisotopic Molecular Weight225.9336826
IUPAC Name4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
Traditional Name4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
CAS Registry NumberNot Available
SMILES
ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O
InChI Identifier
InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
InChI KeyHZNVUJQVZSTENZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentP-benzoquinones
Alternative Parents
Substituents
  • P-benzoquinone
  • Alpha-haloketone
  • Alpha-chloroketone
  • Vinylogous halide
  • Carbonitrile
  • Nitrile
  • Vinyl chloride
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.94ALOGPS
logP1.43ChemAxon
logS-3.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area81.72 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.72 m³·mol⁻¹ChemAxon
Polarizability17.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.80430932474
DeepCCS[M-H]-142.44630932474
DeepCCS[M-2H]-176.4630932474
DeepCCS[M+Na]+151.58730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O2730.0Standard polar33892256
2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O1891.3Standard non polar33892256
2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O1822.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2690000000-963f909398eb93deaa102021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 10V, Positive-QTOFsplash10-004i-0090000000-2f9658568c35d08fea7f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 20V, Positive-QTOFsplash10-004i-0090000000-2f9658568c35d08fea7f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 40V, Positive-QTOFsplash10-004i-9530000000-0edf707ac1b265c039112021-10-12Wishart LabView Spectrum
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 ID6517
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
METLIN IDNot Available
PubChem Compound6775
PDB IDNot Available
ChEBI IDNot Available
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 ]