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Showing NP-Card for 2,6-Dichloro-p-benzohydroquinone (NP0054983)

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Record Information
Version2.0
Created at2022-04-28 01:10:13 UTC
Updated at2022-04-28 01:10:13 UTC
NP-MRD IDNP0054983
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6-Dichloro-p-benzohydroquinone
Description 2,6-Dichloro-p-benzohydroquinone is found in Sphingobium chlorophenolicum. 2,6-Dichloro-p-benzohydroquinone was first documented in 1999 (PMID: 10526172).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054983 (2,6-Dichloro-p-benzohydroquinone)


  Mrv1652304272019292D          

 10 10  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
M  END
Download

3D MOL for NP0054983 (2,6-Dichloro-p-benzohydroquinone)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.7724   -0.4051   -0.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.2006   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9501    1.1051   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    1.3339    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    2.9637    0.1978 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3107    0.2837    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585    0.5731    0.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -0.9974   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -2.3378   -0.0152 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271   -1.2620   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929   -0.5217    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    1.9500   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175   -0.2023    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -2.2827   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10  2  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
 10 14  1  0
M  END
Download

3D SDF for NP0054983 (2,6-Dichloro-p-benzohydroquinone)


  Mrv1652304272019292D          

 10 10  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(Cl)=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H4Cl2O2/c7-4-1-3(9)2-5(8)6(4)10/h1-2,9-10H

> <INCHI_KEY>
QQAHQUBHRBQWBL-UHFFFAOYSA-N

> <FORMULA>
C6H4Cl2O2

> <MOLECULAR_WEIGHT>
179.0

> <EXACT_MASS>
177.9588348

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
15.056907991227018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dichlorobenzene-1,4-diol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.574204525333333

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.829714045517116

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.979123655198743

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565808176450351

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
39.6294

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dichlorohydroquinone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0054983 (2,6-Dichloro-p-benzohydroquinone)

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PDB for NP0054983 (2,6-Dichloro-p-benzohydroquinone)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.540   2.667   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0      -3.080   0.000   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.540   2.667   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    9                                                  
CONECT    4    1    6    7                                                  
CONECT    5    2    6    8                                                  
CONECT    6    4    5   10                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    3                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0054983 (2,6-Dichloro-p-benzohydroquinone)
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SMILES for NP0054983 (2,6-Dichloro-p-benzohydroquinone)
OC1=CC(Cl)=C(O)C(Cl)=C1
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INCHI for NP0054983 (2,6-Dichloro-p-benzohydroquinone)
InChI=1S/C6H4Cl2O2/c7-4-1-3(9)2-5(8)6(4)10/h1-2,9-10H
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View in JSmol
Synonyms
ValueSource
2,6-Dichloro-1,4-benzenediolChEBI
2,6-Dichloro-4-hydroquinoneChEBI
2,6-dichloro-P-HydroquinoneMeSH
2,6-DiCHMeSH
Chemical FormulaC6H4Cl2O2
Average Mass179.0000 Da
Monoisotopic Mass177.95883 Da
IUPAC Name2,6-dichlorobenzene-1,4-diol
Traditional Name2,6-dichlorohydroquinone
CAS Registry NumberNot Available
SMILES
OC1=CC(Cl)=C(O)C(Cl)=C1
InChI Identifier
InChI=1S/C6H4Cl2O2/c7-4-1-3(9)2-5(8)6(4)10/h1-2,9-10H
InChI KeyQQAHQUBHRBQWBL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sphingobium chlorophenolicumBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,4-dihydroxy-2-halobenzenoids. These are aromatic compounds containing a 1,-2-dihydroxybenzene moiety, which carries an halogen atom at the ring 2-position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub Class1,4-dihydroxy-2-halobenzenoids  
Direct Parent1,4-dihydroxy-2-halobenzenoids  
Alternative Parents
Substituents
  • 1,4-dihydroxy-2-halobenzenoid
    • 

  • Chlorohydroquinone
    • 

  • 1,3-dichlorobenzene
    • 

  • 3-halophenol
    • 

  • 2-halophenol
    • 

  • Hydroquinone
    • 

  • 3-chlorophenol
    • 

  • 2-chlorophenol
    • 

  • Chlorobenzene
    • 

  • Halobenzene
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Aryl halide
    • 

  • Aryl chloride
    • 

  • Organohalogen compound
    • 

  • Organochloride
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.65ALOGPS
logP2.57ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.98ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.63 m³·mol⁻¹ChemAxon
Polarizability15.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007487  
Chemspider IDNot Available
KEGG Compound IDC07097  
BioCyc ID26-DICHLORO-P-HYDROQUINONE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88366  
PDB IDNot Available
ChEBI ID27633  
Good Scents IDNot Available
References
General References
  1. Ohtsubo Y, Miyauchi K, Kanda K, Hatta T, Kiyohara H, Senda T, Nagata Y, Mitsui Y, Takagi M: PcpA, which is involved in the degradation of pentachlorophenol in Sphingomonas chlorophenolica ATCC39723, is a novel type of ring-cleavage dioxygenase. FEBS Lett. 1999 Oct 15;459(3):395-8. doi: 10.1016/s0014-5793(99)01305-8. [PubMed:10526172  ] 
  2. Ma H, Wohlers J, Meierhenrich U, Bernecker A, Suling V, Thiemann W: Analysis of oxidative degradation products of 2,4,6-trichlorophenol treated with air ions. Anal Chem. 2001 Jul 15;73(14):3506-10. doi: 10.1021/ac010097n. [PubMed:11476256  ] 
  3. Schmidt S, Kirby GW: Dioxygenative cleavage of C-methylated hydroquinones and 2,6-dichlorohydroquinone by Pseudomonas sp. HH35. Biochim Biophys Acta. 2001 Nov 7;1568(1):83-9. doi: 10.1016/s0304-4165(01)00204-5. [PubMed:11731089  ] 
  4. Brillas E, Garcia-Segura S, Skoumal M, Arias C: Electrochemical incineration of diclofenac in neutral aqueous medium by anodic oxidation using Pt and boron-doped diamond anodes. Chemosphere. 2010 Apr;79(6):605-12. doi: 10.1016/j.chemosphere.2010.03.004. Epub  2010 Mar 21. [PubMed:20307900  ] 
  5. Machonkin TE, Doerner AE: Substrate specificity of Sphingobium chlorophenolicum 2,6-dichlorohydroquinone 1,2-dioxygenase. Biochemistry. 2011 Oct 18;50(41):8899-913. doi: 10.1021/bi200855m. Epub 2011 Sep  26. [PubMed:21870805  ]