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Showing NP-Card for 4-Chlorocatechol (NP0002732)

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Record Information
Version1.0
Created at2020-11-23 19:39:03 UTC
Updated at2021-08-12 19:51:59 UTC
NP-MRD IDNP0002732
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorocatechol
Provided ByBMRBBMRB logo
Description4-Chlorocatechol 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. 4-Chlorocatechol 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 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 4-Chlorocatechol (PMID: 23261399) (PMID: 24057966) (PMID: 24064298) (PMID: 25880455).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002732 (4-Chlorocatechol)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.0413   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    1.5000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -0.7500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567   -3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404    0.7500    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  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
Download

3D MOL for NP0002732 (4-Chlorocatechol)

NP0002732
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.2258    1.1541    0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.6076    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788    1.3950    0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4430    0.8580   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -0.5003   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -1.1552   -0.4083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.2955   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.7449   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203   -1.5304   -0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    2.1509    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554    2.4655    0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    1.4854   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055   -2.3712   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -2.5191   -0.1676 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  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
Download

3D SDF for NP0002732 (4-Chlorocatechol)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.0413   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    1.5000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -0.7500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567   -3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404    0.7500    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  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
> <DATABASE_ID>
NP0002732

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
WWOBYPKUYODHDG-UHFFFAOYSA-N

> <FORMULA>
C6H5ClO2

> <MOLECULAR_WEIGHT>
144.556

> <EXACT_MASS>
143.997807111

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.918552350202802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.9701598489999999

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.083518697574103

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.667906631147677

> <JCHEM_PKA_STRONGEST_BASIC>
-6.592068932148709

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
34.8246

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chlorocatechol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002732 (4-Chlorocatechol)

NP0002732
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.2258    1.1541    0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.6076    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788    1.3950    0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4430    0.8580   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -0.5003   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -1.1552   -0.4083 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.2955   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.7449   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203   -1.5304   -0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    2.1509    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554    2.4655    0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    1.4854   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055   -2.3712   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -2.5191   -0.1676 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  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
Download

PDB for NP0002732 (4-Chlorocatechol)

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         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       1.334   2.310   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  -2.310   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0002732 (4-Chlorocatechol)

COMPND    NP0002732
HETATM    1  O1  UNL     1      -2.226   1.154   0.326  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.953   0.608   0.154  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.179   1.395   0.159  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.443   0.858  -0.011  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.627  -0.500  -0.196  1.00  0.00           C  
HETATM    6 CL1  UNL     1       3.228  -1.155  -0.408  1.00  0.00          CL  
HETATM    7  C5  UNL     1       0.499  -1.295  -0.202  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.755  -0.745  -0.031  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.920  -1.530  -0.033  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.328   2.151   0.458  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.055   2.466   0.302  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.328   1.485  -0.006  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.606  -2.371  -0.345  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.781  -2.519  -0.168  1.00  0.00           H  
CONECT    1    2   10
CONECT    2    3    3    8
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    7    8    8   13
CONECT    8    9
CONECT    9   14
END
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SMILES for NP0002732 (4-Chlorocatechol)

OC1=C(O)C=C(Cl)C=C1
Download

INCHI for NP0002732 (4-Chlorocatechol)

InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H
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View in JSmol
Synonyms
ValueSource
4-Chloro-1,2-benzenediolChEBI
4-ChloropyrocatecholChEBI
4-Chloro-benzene-1,2-diolHMDB
4-Chloro-pyrocatecholHMDB
4-Chlorobenzene-1,2-diolHMDB
Chemical FormulaC6H5ClO2
Average Mass144.5560 Da
Monoisotopic Mass143.99781 Da
IUPAC Name4-chlorobenzene-1,2-diol
Traditional Name4-chlorocatechol
CAS Registry NumberNot Available
SMILES
OC1=C(O)C=C(Cl)C=C1
InChI Identifier
InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H
InChI KeyWWOBYPKUYODHDG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.61ALOGPS
logP1.97ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.82 m³·mol⁻¹ChemAxon
Polarizability12.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041810
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15638
KEGG Compound IDC02375
BioCyc IDCPD-9152
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16496
PDB ID4CL
ChEBI ID27772
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. 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 ]
  3. Arora PK, Srivastava A, Singh VP: Novel degradation pathway of 4-chloro-2-aminophenol via 4-chlorocatechol in Burkholderia sp. RKJ 800. Environ Sci Pollut Res Int. 2014 Feb;21(3):2298-2304. doi: 10.1007/s11356-013-2167-y. Epub 2013 Sep 21. [PubMed:24057966 ]
  4. Nitisakulkan T, Oku S, Kudo D, Nakashimada Y, Tajima T, Vangnai AS, Kato J: Degradation of chloroanilines by toluene dioxygenase from Pseudomonas putida T57. J Biosci Bioeng. 2014 Mar;117(3):292-7. doi: 10.1016/j.jbiosc.2013.08.012. Epub 2013 Sep 21. [PubMed:24064298 ]
  5. Ding J, Su M, Wu C, Lin K: Transformation of triclosan to 2,8-dichlorodibenzo-p-dioxin by iron and manganese oxides under near dry conditions. Chemosphere. 2015 Aug;133:41-6. doi: 10.1016/j.chemosphere.2015.03.055. Epub 2015 Apr 13. [PubMed:25880455 ]