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Showing NP-Card for 4-Chlorophenol (NP0002747)

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Record Information
Version2.0
Created at2020-11-23 19:39:24 UTC
Updated at2021-08-19 23:59:19 UTC
NP-MRD IDNP0002747
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorophenol
Provided ByBMRBBMRB logo
Description4-Chlorophenol, also known as parachlorophenol, belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring. 4-Chlorophenol is a drug which is used as an intermediate in organic synthesis of dyes and drugs. Local antibacterial agent in root canal therapy, as topical antiseptic in ointments. 4-Chlorophenol exists in all living organisms, ranging from bacteria to humans. 4-Chlorophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Chlorophenol was first documented in 2000 (PMID: 10848923). Based on a literature review a small amount of articles have been published on 4-Chlorophenol (PMID: 24279624) (PMID: 24390833) (PMID: 24473310).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002747 (4-Chlorophenol)


     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.5295   -0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8286    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888    1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    0.9820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4392   -0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218   -1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625    1.9640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722    2.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5731   -1.9640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2617   -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  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

3D MOL for NP0002747 (4-Chlorophenol)

NP0002747
     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    2.5747   -0.1001   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.0262   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    1.1728   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715    1.2039   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.0567   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3978    0.1184   -0.0096 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637   -1.1465   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -1.1698   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -0.1562    0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236    2.0712   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948    2.1598    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5441   -2.0600   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -2.1241   -0.1582 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  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

3D SDF for NP0002747 (4-Chlorophenol)


     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.5295   -0.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8286    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888    1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    0.9820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4392   -0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218   -1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625    1.9640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722    2.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5731   -1.9640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2617   -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  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
> <DATABASE_ID>
NP0002747

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H

> <INCHI_KEY>
WXNZTHHGJRFXKQ-UHFFFAOYSA-N

> <FORMULA>
C6H5ClO

> <MOLECULAR_WEIGHT>
128.556

> <EXACT_MASS>
128.002892489

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
12.024294368266357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-chlorophenol

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.2737251706666664

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.963636620612126

> <JCHEM_PKA_STRONGEST_BASIC>
-6.261855903181934

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
32.8437

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorophenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002747 (4-Chlorophenol)

NP0002747
     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    2.5747   -0.1001   -0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.0262   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    1.1728   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715    1.2039   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.0567   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3978    0.1184   -0.0096 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637   -1.1465   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -1.1698   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -0.1562    0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236    2.0712   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948    2.1598    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5441   -2.0600   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -2.1241   -0.1582 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  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

PDB for NP0002747 (4-Chlorophenol)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   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   1.540   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 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0002747 (4-Chlorophenol)

COMPND    NP0002747
HETATM    1  O1  UNL     1       2.575  -0.100  -0.116  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.185  -0.026  -0.090  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.506   1.173  -0.038  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.872   1.204  -0.014  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.638   0.057  -0.041  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -3.398   0.118  -0.010  1.00  0.00          CL  
HETATM    7  C5  UNL     1      -0.964  -1.146  -0.093  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.414  -1.170  -0.117  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.059  -0.156   0.782  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.124   2.071  -0.018  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.395   2.160   0.027  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.544  -2.060  -0.115  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.948  -2.124  -0.158  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    3    8
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    7    8    8   12
CONECT    8   13
END
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SMILES for NP0002747 (4-Chlorophenol)

OC1=CC=C(Cl)C=C1
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INCHI for NP0002747 (4-Chlorophenol)

InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
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View in JSmol
Synonyms
ValueSource
p-ChlorophenolChEBI
ParachlorophenolChEBI
4-Chlorophenol ion (1+)HMDB
4-Chlorophenol, nickel (+2) saltHMDB
4-Chlorophenol, titanium (+4) saltHMDB
4-ChlorophenoxideHMDB
Para-monochlorophenolHMDB
4-Chlorophenol, copper (+1) saltHMDB
4-MonochlorophenolHMDB
4-Chlorophenol, potassium saltHMDB
4-Chlorophenol, sodium saltHMDB
Chemical FormulaC6H5ClO
Average Mass128.5560 Da
Monoisotopic Mass128.00289 Da
IUPAC Name4-chlorophenol
Traditional Namechlorophenol
CAS Registry NumberNot Available
SMILES
OC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
InChI KeyWXNZTHHGJRFXKQ-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 p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassHalophenols
Direct ParentP-chlorophenols
Alternative Parents
Substituents
  • 4-chlorophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point42.70 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point220.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3222 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.390The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.37ALOGPS
logP2.27ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.84 m³·mol⁻¹ChemAxon
Polarizability12.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246398
DrugBank IDDB13154
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13875219
KEGG Compound IDC02124
BioCyc IDCPD-10870
BiGG IDNot Available
Wikipedia Link4-Chlorophenol
METLIN IDNot Available
PubChem Compound4684
PDB IDNot Available
ChEBI ID28078
Good Scents IDrw1201641
References
General References
  1. Pham NH, Weiner JM, Reisner GS, Baldo BA: Anaphylaxis to chlorhexidine. Case report. Implication of immunoglobulin E antibodies and identification of an allergenic determinant. Clin Exp Allergy. 2000 Jul;30(7):1001-7. doi: 10.1046/j.1365-2222.2000.00887.x. [PubMed:10848923 ]
  2. Qi L, Yao J, You H, Zhang R, Feng C, Van Agtmaal S: Oxidation products and degradation pathways of 4-chlorophenol by catalytic ozonation with MnOx/gamma-Al2O3/TiO2 as catalyst in aqueous solution. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2014;49(3):327-37. doi: 10.1080/10934529.2014.846657. [PubMed:24279624 ]
  3. El-Sayed WS, Ibrahim MK, Ouf SA: Molecular characterization of the alpha subunit of multicomponent phenol hydroxylase from 4-chlorophenol-degrading Pseudomonas sp. strain PT3. J Microbiol. 2014 Jan;52(1):13-9. doi: 10.1007/s12275-014-3250-x. Epub 2014 Jan 4. [PubMed:24390833 ]
  4. Mihoc G, Ianos R, Pacurariu C: Adsorption of phenol and p-chlorophenol from aqueous solutions by magnetic nanopowder. Water Sci Technol. 2014;69(2):385-91. doi: 10.2166/wst.2013.727. [PubMed:24473310 ]