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Showing NP-Card for 4-Chlorophenol (NP0002747)

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Record Information
Version1.0
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. It was first documented in 2000 (PMID: 10848923). Based on a literature review a significant number of articles have been published on 4-Chlorophenol (PMID: 17984079) (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. 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. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]