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Showing NP-Card for 3,5-Dichlorocatechol (NP0002703)

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Record Information
Version1.0
Created at2020-11-23 19:38:20 UTC
Updated at2021-08-12 19:51:54 UTC
NP-MRD IDNP0002703
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-Dichlorocatechol
Provided ByBMRBBMRB logo
Description3,5-Dichlorocatechol belongs to the class of organic compounds known as 4-chlorocatechols. These are chlorocatechols with the chlorine atom attached at position C4 of the benzene ring. It was first documented in 2006 (PMID: 16637006). Based on a literature review a significant number of articles have been published on 3,5-dichlorocatechol (PMID: 17984079) (PMID: 23409454) (PMID: 23261399) (PMID: 28434228) (PMID: 25559487) (PMID: 20040374).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002703 (3,5-Dichlorocatechol)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    1.4730   -2.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910   -1.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9640   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.5669    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    1.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    2.8347    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9820    0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4550    0.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -1.9843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -2.8347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    2.2678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    1.9843    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
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  6 13  1  0
 10 14  1  0
M  END
Download

3D MOL for NP0002703 (3,5-Dichlorocatechol)

NP0002703
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.2699   -0.6956   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.3744   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -1.3494   -0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096   -1.0237    0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493   -2.2712    0.0930 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    0.3154    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    1.2844    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    2.9952    0.1767 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    0.9683   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664    1.9636   -0.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -1.6827   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969   -2.3919   -0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.5880    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    1.6739   -0.1058 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
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  6 13  1  0
 10 14  1  0
M  END
Download

3D SDF for NP0002703 (3,5-Dichlorocatechol)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    1.4730   -2.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910   -1.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9640   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.5669    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    1.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    2.8347    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9820    0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4550    0.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -1.9843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -2.8347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    2.2678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    1.9843    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
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  6 13  1  0
 10 14  1  0
M  END
> <DATABASE_ID>
NP0002703

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(Cl)=CC(Cl)=C1O

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

> <INCHI_KEY>
XSXYVLIPQMXCBV-UHFFFAOYSA-N

> <FORMULA>
C6H4Cl2O2

> <MOLECULAR_WEIGHT>
179.001

> <EXACT_MASS>
177.958834786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.09344574441417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dichlorobenzene-1,2-diol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.574204525333333

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.070259637278125

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.569552270410058

> <JCHEM_PKA_STRONGEST_BASIC>
-6.976633469644612

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
39.6294

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dichlorocatechol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002703 (3,5-Dichlorocatechol)

NP0002703
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.2699   -0.6956   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.3744   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -1.3494   -0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096   -1.0237    0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493   -2.2712    0.0930 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    0.3154    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    1.2844    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    2.9952    0.1767 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    0.9683   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664    1.9636   -0.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5203   -1.6827   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969   -2.3919   -0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.5880    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    1.6739   -0.1058 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
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  3 12  1  0
  6 13  1  0
 10 14  1  0
M  END
Download

PDB for NP0002703 (3,5-Dichlorocatechol)

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    7                                                  
CONECT    4    1    6    8                                                  
CONECT    5    2    6    9                                                  
CONECT    6    4    5   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 NP0002703 (3,5-Dichlorocatechol)

COMPND    NP0002703
HETATM    1  O1  UNL     1       2.270  -0.696  -0.170  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.903  -0.374  -0.071  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.072  -1.349  -0.041  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.410  -1.024   0.056  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -2.649  -2.271   0.093  1.00  0.00          CL  
HETATM    6  C4  UNL     1      -1.735   0.315   0.122  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.752   1.284   0.092  1.00  0.00           C  
HETATM    8 CL2  UNL     1      -1.162   2.995   0.177  1.00  0.00          CL  
HETATM    9  C6  UNL     1       0.588   0.968  -0.005  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.566   1.964  -0.034  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.520  -1.683  -0.219  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.197  -2.392  -0.094  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.798   0.588   0.200  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.533   1.674  -0.106  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   13
CONECT    7    8    9    9
CONECT    9   10
CONECT   10   14
END
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SMILES for NP0002703 (3,5-Dichlorocatechol)

OC1=CC(Cl)=CC(Cl)=C1O
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INCHI for NP0002703 (3,5-Dichlorocatechol)

InChI=1S/C6H4Cl2O2/c7-3-1-4(8)6(10)5(9)2-3/h1-2,9-10H
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View in JSmol
Synonyms
ValueSource
1,2-Dihydroxy-4,6-dichlorobenzeneChEBI
Chemical FormulaC6H4Cl2O2
Average Mass179.0010 Da
Monoisotopic Mass177.95883 Da
IUPAC Name3,5-dichlorobenzene-1,2-diol
Traditional Name3,5-dichlorocatechol
CAS Registry NumberNot Available
SMILES
OC1=CC(Cl)=CC(Cl)=C1O
InChI Identifier
InChI=1S/C6H4Cl2O2/c7-3-1-4(8)6(10)5(9)2-3/h1-2,9-10H
InChI KeyXSXYVLIPQMXCBV-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-chlorocatechols. These are chlorocatechols with the chlorine atom attached at position C4 of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct Parent4-chlorocatechols
Alternative Parents
Substituents
  • 3-chlorocatechol
  • 4-chlorocatechol
  • 4-chlorophenol
  • 1,3-dichlorobenzene
  • 2-chlorophenol
  • 3-chlorophenol
  • 2-halophenol
  • 3-halophenol
  • 4-halophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • 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
logP2.68ALOGPS
logP2.57ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.57ChemAxon
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 ID24384
KEGG Compound IDC02933
BioCyc ID35-DICHLOROCATECHOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15788
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. Benndorf D, Thiersch M, Loffhagen N, Kunath C, Harms H: Pseudomonas putida KT2440 responds specifically to chlorophenoxy herbicides and their initial metabolites. Proteomics. 2006 Jun;6(11):3319-29. doi: 10.1002/pmic.200500781. [PubMed:16637006 ]
  3. Choudhary AK, Kumar S, Sharma C: Removal of chlorophenolics from pulp and paper mill wastewater through constructed wetland. Water Environ Res. 2013 Jan;85(1):54-62. doi: 10.2175/106143012x13415215907419. [PubMed:23409454 ]
  4. Ferraroni M, Kolomytseva M, Scozzafava A, Golovleva L, Briganti F: X-ray structures of 4-chlorocatechol 1,2-dioxygenase adducts with substituted catechols: new perspectives in the molecular basis of intradiol ring cleaving dioxygenases specificity. J Struct Biol. 2013 Mar;181(3):274-82. doi: 10.1016/j.jsb.2012.11.007. Epub 2012 Dec 20. [PubMed:23261399 ]
  5. Wu X, Wang W, Liu J, Pan D, Tu X, Lv P, Wang Y, Cao H, Wang Y, Hua R: Rapid Biodegradation of the Herbicide 2,4-Dichlorophenoxyacetic Acid by Cupriavidus gilardii T-1. J Agric Food Chem. 2017 May 10;65(18):3711-3720. doi: 10.1021/acs.jafc.7b00544. Epub 2017 May 1. [PubMed:28434228 ]
  6. Zhang C, Zhou M, Ren G, Yu X, Ma L, Yang J, Yu F: Heterogeneous electro-Fenton using modified iron-carbon as catalyst for 2,4-dichlorophenol degradation: influence factors, mechanism and degradation pathway. Water Res. 2015 Mar 1;70:414-24. doi: 10.1016/j.watres.2014.12.022. Epub 2014 Dec 20. [PubMed:25559487 ]
  7. Matera I, Ferraroni M, Kolomytseva M, Golovleva L, Scozzafava A, Briganti F: Catechol 1,2-dioxygenase from the Gram-positive Rhodococcus opacus 1CP: quantitative structure/activity relationship and the crystal structures of native enzyme and catechols adducts. J Struct Biol. 2010 Jun;170(3):548-64. doi: 10.1016/j.jsb.2009.12.023. Epub 2009 Dec 28. [PubMed:20040374 ]