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Showing NP-Card for 2,5-Dichlorohydroquinone (NP0002837)

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Record Information
Version1.0
Created at2020-11-23 19:41:40 UTC
Updated at2021-08-12 19:52:17 UTC
NP-MRD IDNP0002837
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5-Dichlorohydroquinone
Provided ByBMRBBMRB logo
Description2,5-Dichlorohydroquinone is also known as 2,5-dichloro-1,4-benzenediol. 2,5-Dichlorohydroquinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2002 (PMID: 11872169). Based on a literature review a significant number of articles have been published on 2,5-dichlorohydroquinone (PMID: 17984079) (PMID: 17578411) (PMID: 29934333) (PMID: 25981800).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002837 (2,5-Dichlorohydroquinone)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.8347   -0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339   -0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678   -1.9640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4174    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347    0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678    1.9640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5669   -2.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    2.9459    0.0000 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  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

3D MOL for NP0002837 (2,5-Dichlorohydroquinone)

NP0002837
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7600    0.0513   -0.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.0197   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7541    0.1914    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169    0.1590    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.3800    2.6616 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3804   -0.0586   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7574   -0.0935    0.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7793   -0.2361   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -0.1975   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -0.4220   -2.9091 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3121    0.2149    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    0.3620    1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950    0.0335    1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051   -0.4041   -2.0938 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  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

3D SDF for NP0002837 (2,5-Dichlorohydroquinone)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.8347   -0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339   -0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678   -1.9640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4174    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347    0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678    1.9640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5669   -2.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    2.9459    0.0000 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  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
M  END
> <DATABASE_ID>
NP0002837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(Cl)=C(O)C=C1Cl

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

> <INCHI_KEY>
AYNPIRVEWMUJDE-UHFFFAOYSA-N

> <FORMULA>
C6H4Cl2O2

> <MOLECULAR_WEIGHT>
179.0

> <EXACT_MASS>
177.9588348

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
15.090135976296281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dichlorobenzene-1,4-diol

> <JCHEM_LOGP>
2.574204525333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.26743462929308

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.478104924789655

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9939380159280224

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
39.6294

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dichlorohydroquinone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002837 (2,5-Dichlorohydroquinone)

NP0002837
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7600    0.0513   -0.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.0197   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7541    0.1914    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169    0.1590    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.3800    2.6616 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3804   -0.0586   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7574   -0.0935    0.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7793   -0.2361   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -0.1975   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -0.4220   -2.9091 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3121    0.2149    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    0.3620    1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950    0.0335    1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051   -0.4041   -2.0938 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  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

PDB for NP0002837 (2,5-Dichlorohydroquinone)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   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       1.334  -0.770   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    6    7                                                  
CONECT    4    2    5    8                                                  
CONECT    5    1    4    9                                                  
CONECT    6    2    3   10                                                  
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002837 (2,5-Dichlorohydroquinone)

COMPND    NP0002837
HETATM    1  O1  UNL     1       2.760   0.051  -0.390  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.375   0.020  -0.230  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.754   0.191   0.969  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.617   0.159   1.121  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -1.406   0.380   2.662  1.00  0.00          CL  
HETATM    6  C4  UNL     1      -1.380  -0.059  -0.005  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.757  -0.093   0.134  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.779  -0.236  -1.234  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.611  -0.197  -1.353  1.00  0.00           C  
HETATM   10 CL2  UNL     1       1.376  -0.422  -2.909  1.00  0.00          CL  
HETATM   11  H1  UNL     1       3.312   0.215   0.462  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.352   0.362   1.852  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.195   0.033   1.015  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.405  -0.404  -2.094  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3    3    9
CONECT    3    4   12
CONECT    4    5    6    6
CONECT    6    7    8
CONECT    7   13
CONECT    8    9    9   14
CONECT    9   10
END
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SMILES for NP0002837 (2,5-Dichlorohydroquinone)

OC1=CC(Cl)=C(O)C=C1Cl
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INCHI for NP0002837 (2,5-Dichlorohydroquinone)

InChI=1S/C6H4Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2,9-10H
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View in JSmol
Synonyms
ValueSource
2,5-Dichloro-1,4-benzenediolChEBI
2,5-Dichloro-1,4-hydroquinoneChEBI
2,5-Dichloro-p-benzohydroquinoneChEBI
2,5-Dichloro-p-hydroquinoneChEBI
2,5-DCHMeSH
2,5-DCHQMeSH
Chemical FormulaC6H4Cl2O2
Average Mass179.0000 Da
Monoisotopic Mass177.95883 Da
IUPAC Name2,5-dichlorobenzene-1,4-diol
Traditional Name2,5-dichlorohydroquinone
CAS Registry NumberNot Available
SMILES
OC1=CC(Cl)=C(O)C=C1Cl
InChI Identifier
InChI=1S/C6H4Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2,9-10H
InChI KeyAYNPIRVEWMUJDE-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP2.57ChemAxon
pKa (Strongest Acidic)7.48ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.63 m³·mol⁻¹ChemAxon
Polarizability15.09 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 IDNot Available
Chemspider ID64
KEGG Compound IDC06600
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27545
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Lee HS, Miyauchi K, Nagata Y, Fukuda R, Sasagawa S, Endoh H, Kato S, Horiuchi H, Takagi M, Ohta A: Employment of the human estrogen receptor beta ligand-binding domain and co-activator SRC1 nuclear receptor-binding domain for the construction of a yeast two-hybrid detection system for endocrine disrupters. J Biochem. 2002 Mar;131(3):399-405. doi: 10.1093/oxfordjournals.jbchem.a003115. [PubMed:11872169 ]
  3. Manickam N, Misra R, Mayilraj S: A novel pathway for the biodegradation of gamma-hexachlorocyclohexane by a Xanthomonas sp. strain ICH12. J Appl Microbiol. 2007 Jun;102(6):1468-78. doi: 10.1111/j.1365-2672.2006.03209.x. [PubMed:17578411 ]
  4. Li N, Tong RL, Yao L, Chen Q, Yan X, Ding DR, Qiu JG, He J, Jiang JD: Roles of Two Glutathione-Dependent 3,6-Dichlorogentisate Dehalogenases in Rhizorhabdus dicambivorans Ndbn-20 in the Catabolism of the Herbicide Dicamba. Appl Environ Microbiol. 2018 Aug 17;84(17). pii: AEM.00623-18. doi: 10.1128/AEM.00623-18. Print 2018 Sep 1. [PubMed:29934333 ]
  5. Maharana D, Xu Z, Niu J, Rao NN: Electrochemical oxidation of 2,4,5-trichlorophenoxyacetic acid by metal-oxide-coated Ti electrodes. Chemosphere. 2015 Oct;136:145-52. doi: 10.1016/j.chemosphere.2015.04.100. Epub 2015 May 15. [PubMed:25981800 ]