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Showing NP-Card for Chlorohydroquinone (NP0002708)

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Record Information
Version1.0
Created at2020-11-23 19:38:27 UTC
Updated at2021-08-12 19:51:55 UTC
NP-MRD IDNP0002708
Secondary Accession NumbersNone
Natural Product Identification
Common NameChlorohydroquinone
Provided ByBMRBBMRB logo
DescriptionChlorohydroquinone, also known as chloroquinol, 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. Chlorohydroquinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Chlorohydroquinone is found in Streptomyces rochei. It was first documented in 2002 (PMID: 11872169). Based on a literature review a small amount of articles have been published on chlorohydroquinone (PMID: 17984079) (PMID: 20050667) (PMID: 21960016) (PMID: 34150263) (PMID: 32310122) (PMID: 29332277).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002708 (Chlorohydroquinone)


     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
   -1.1339    0.9820    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
    1.4174    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
    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
   -0.2835   -1.4730    0.0000 C   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
   -2.2678    1.9640    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  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  9 14  1  0
M  END
Download

3D MOL for NP0002708 (Chlorohydroquinone)

NP0002708
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7200    0.6635   -0.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    0.3352   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679   -0.9383    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3501   -1.2742    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415   -0.3267    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937   -0.6198    0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9371    0.9476   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.1616   -0.4082 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.2864   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090    0.9892    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.6932    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802   -2.2831    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -1.5636    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    2.3153   -0.6664 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  9 14  1  0
M  END
Download

3D SDF for NP0002708 (Chlorohydroquinone)


     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
   -1.1339    0.9820    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
    1.4174    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
    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
   -0.2835   -1.4730    0.0000 C   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
   -2.2678    1.9640    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  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  9 14  1  0
M  END
> <DATABASE_ID>
NP0002708

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO2/c7-5-3-4(8)1-2-6(5)9/h1-3,8-9H

> <INCHI_KEY>
AJPXTSMULZANCB-UHFFFAOYSA-N

> <FORMULA>
C6H5ClO2

> <MOLECULAR_WEIGHT>
144.55

> <EXACT_MASS>
143.9978071

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
12.881121179346312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chlorobenzene-1,4-diol

> <JCHEM_LOGP>
1.9701598489999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.586302158847708

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.390006773338163

> <JCHEM_PKA_STRONGEST_BASIC>
-6.22653076254189

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
34.8246

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
chlorohydroquinone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002708 (Chlorohydroquinone)

NP0002708
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7200    0.6635   -0.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    0.3352   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679   -0.9383    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3501   -1.2742    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415   -0.3267    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937   -0.6198    0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9371    0.9476   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.1616   -0.4082 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.2864   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090    0.9892    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.6932    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802   -2.2831    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -1.5636    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    2.3153   -0.6664 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  9 14  1  0
M  END
Download

PDB for NP0002708 (Chlorohydroquinone)

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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    1    3    8                                                  
CONECT    5    3    6    7                                                  
CONECT    6    2    5    9                                                  
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002708 (Chlorohydroquinone)

COMPND    NP0002708
HETATM    1  O1  UNL     1       2.720   0.663  -0.430  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.379   0.335  -0.249  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.968  -0.938   0.086  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.350  -1.274   0.268  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.341  -0.327   0.118  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.694  -0.620   0.292  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.937   0.948  -0.216  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -2.203   2.162  -0.408  1.00  0.00          CL  
HETATM    9  C6  UNL     1       0.391   1.286  -0.399  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.309   0.989   0.325  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.731  -1.693   0.207  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.680  -2.283   0.534  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.965  -1.564   0.538  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.674   2.315  -0.666  1.00  0.00           H  
CONECT    1    2   10
CONECT    2    3    3    9
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    6   13
CONECT    7    8    9    9
CONECT    9   14
END
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SMILES for NP0002708 (Chlorohydroquinone)

OC1=CC(Cl)=C(O)C=C1
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INCHI for NP0002708 (Chlorohydroquinone)

InChI=1S/C6H5ClO2/c7-5-3-4(8)1-2-6(5)9/h1-3,8-9H
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View in JSmol
Synonyms
ValueSource
1,4-Dihydroxyl-2-chlorobenzeneChEBI
2,5-DihydroxychlorobenzeneChEBI
2-Chloro-1,4-benzenediolChEBI
2-ChlorohydroquinoneChEBI
ChloroquinolChEBI
MonochlorohydroquinoneChEBI
2-Chloro-1,4-hydroxyquinoneMeSH
Chemical FormulaC6H5ClO2
Average Mass144.5500 Da
Monoisotopic Mass143.99781 Da
IUPAC Name2-chlorobenzene-1,4-diol
Traditional Namechlorohydroquinone
CAS Registry NumberNot Available
SMILES
OC1=CC(Cl)=C(O)C=C1
InChI Identifier
InChI=1S/C6H5ClO2/c7-5-3-4(8)1-2-6(5)9/h1-3,8-9H
InChI KeyAJPXTSMULZANCB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces rocheiLOTUS Database
Species Where Detected
Species NameSourceReference
Sphingobium chlorophenolicumKNApSAcK Database
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
  • 3-halophenol
  • 2-halophenol
  • Hydroquinone
  • 3-chlorophenol
  • 2-chlorophenol
  • Chlorobenzene
  • Halobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aryl halide
  • Aryl chloride
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen 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
logP1.97ChemAxon
pKa (Strongest Acidic)8.39ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.82 m³·mol⁻¹ChemAxon
Polarizability12.88 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 IDC00007485
Chemspider ID295
KEGG Compound IDC06601
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27675
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. Ghosh A, Khurana M, Chauhan A, Takeo M, Chakraborti AK, Jain RK: Degradation of 4-nitrophenol, 2-chloro-4-nitrophenol, and 2,4-dinitrophenol by Rhodococcus imtechensis strain RKJ300. Environ Sci Technol. 2010 Feb 1;44(3):1069-77. doi: 10.1021/es9034123. [PubMed:20050667 ]
  4. Arora PK, Jain RK: Pathway for degradation of 2-chloro-4-nitrophenol in Arthrobacter sp. SJCon. Curr Microbiol. 2011 Dec;63(6):568-73. doi: 10.1007/s00284-011-0022-2. Epub 2011 Sep 30. [PubMed:21960016 ]
  5. Mehralipour J, Kermani M: Ultrasonic coupling with electrical current to effective activation of Persulfate for 2, 4 Dichlorophenoxyacetic acid herbicide degradation: modeling, synergistic effect, and a by-product study. J Environ Health Sci Eng. 2021 Mar 29;19(1):625-639. doi: 10.1007/s40201-021-00633-w. eCollection 2021 Jun. [PubMed:34150263 ]
  6. Forti JC, Loretti GH, Tadayozzi YS, de Andrade AR: A phytotoxicity assessment of the efficiency 2,4-D degradation by different oxidative processes. J Environ Manage. 2020 Jul 15;266:110588. doi: 10.1016/j.jenvman.2020.110588. Epub 2020 Apr 15. [PubMed:32310122 ]
  7. Tian H, Ma YJ, Li WY, Wang JW: Efficient degradation of triclosan by an endophytic fungus Penicillium oxalicum B4. Environ Sci Pollut Res Int. 2018 Mar;25(9):8963-8975. doi: 10.1007/s11356-017-1186-5. Epub 2018 Jan 13. [PubMed:29332277 ]