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Showing NP-Card for 2,4,6-Trichlorophenol (NP0002845)

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Record Information
Version2.0
Created at2020-11-23 19:41:52 UTC
Updated at2021-08-12 19:52:18 UTC
NP-MRD IDNP0002845
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4,6-Trichlorophenol
Provided ByBMRBBMRB logo
Description2,4,6-Trichlorophenol is also known as 2,4,6-TCP. 2,4,6-Trichlorophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2,4,6-Trichlorophenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. 2,4,6-Trichlorophenol is found in Carica papaya . 2,4,6-Trichlorophenol was first documented in 2011 (PMID: 21863115). Based on a literature review a small amount of articles have been published on 2,4,6-Trichlorophenol (PMID: 22748215) (PMID: 23995979) (PMID: 24078273).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002845 (2,4,6-Trichlorophenol)


     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
   -1.9625    1.9640    0.0000 Cl  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
   -0.2617   -2.9459    0.0000 Cl  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
    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
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  5 12  1  0
  8 13  1  0
M  END
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3D MOL for NP0002845 (2,4,6-Trichlorophenol)

NP0002845
     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4922   -0.0882   -0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -0.0435   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164   -1.2322   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132   -2.7306   -0.1760 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -1.2478   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.0599    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -0.0432    0.1000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9994    1.1209    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    1.1357    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091    2.6276    0.0928 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    0.7082   -0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -2.2061   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358    2.0591    0.1489 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  5 12  1  0
  8 13  1  0
M  END
Download

3D SDF for NP0002845 (2,4,6-Trichlorophenol)


     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
   -1.9625    1.9640    0.0000 Cl  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
   -0.2617   -2.9459    0.0000 Cl  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
    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
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  5 12  1  0
  8 13  1  0
M  END
> <DATABASE_ID>
NP0002845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(Cl)C=C(Cl)C=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

> <INCHI_KEY>
LINPIYWFGCPVIE-UHFFFAOYSA-N

> <FORMULA>
C6H3Cl3O

> <MOLECULAR_WEIGHT>
197.446

> <EXACT_MASS>
195.924947839

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.377097619809525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,6-trichlorophenol

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.4818145233333335

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.99139224733549

> <JCHEM_PKA_STRONGEST_BASIC>
-7.7957789662152175

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
42.4533

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,6-trichlorophenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002845 (2,4,6-Trichlorophenol)

NP0002845
     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4922   -0.0882   -0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -0.0435   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164   -1.2322   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132   -2.7306   -0.1760 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -1.2478   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.0599    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -0.0432    0.1000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9994    1.1209    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    1.1357    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091    2.6276    0.0928 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    0.7082   -0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -2.2061   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358    2.0591    0.1489 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  5 12  1  0
  8 13  1  0
M  END
Download

PDB for NP0002845 (2,4,6-Trichlorophenol)

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       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       1.334  -0.770   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      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002845 (2,4,6-Trichlorophenol)

COMPND    NP0002845
HETATM    1  O1  UNL     1      -2.492  -0.088  -0.079  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.110  -0.043  -0.035  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.416  -1.232  -0.074  1.00  0.00           C  
HETATM    4 CL1  UNL     1      -1.313  -2.731  -0.176  1.00  0.00          CL  
HETATM    5  C3  UNL     1       0.979  -1.248  -0.033  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.687  -0.060   0.047  1.00  0.00           C  
HETATM    7 CL2  UNL     1       3.435  -0.043   0.100  1.00  0.00          CL  
HETATM    8  C5  UNL     1       0.999   1.121   0.086  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.391   1.136   0.045  1.00  0.00           C  
HETATM   10 CL3  UNL     1      -1.309   2.628   0.093  1.00  0.00          CL  
HETATM   11  H1  UNL     1      -3.100   0.708  -0.057  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.497  -2.206  -0.066  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.536   2.059   0.149  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    8    9    9   13
CONECT    9   10
END
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SMILES for NP0002845 (2,4,6-Trichlorophenol)

OC1=C(Cl)C=C(Cl)C=C1Cl
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INCHI for NP0002845 (2,4,6-Trichlorophenol)

InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
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View in JSmol
Synonyms
ValueSource
1,3,5-Trichloro-2-hydroxybenzeneChEBI
2,4,6-TCPChEBI
2,4,6-Trichlorophenol, 14C-labeledMeSH
2,4,6-Trichlorophenol, copper(+1) saltMeSH
2,4,6-Trichlorophenol, potassium saltMeSH
2,4,6-Trichlorophenol, ZN saltMeSH
2,4,6-Trichlorophenol, nickel(+2) saltMeSH
2,4,6-Trichlorophenol, copper(+2) saltMeSH
2,4,6-Trichlorophenol, sodium saltMeSH
2,4,6-Trichloro-1-hydroxybenzeneMeSH
Sodium 2,4,6-trichlorophenoxideMeSH
Chemical FormulaC6H3Cl3O
Average Mass197.4460 Da
Monoisotopic Mass195.92495 Da
IUPAC Name2,4,6-trichlorophenol
Traditional Name2,4,6-trichlorophenol
CAS Registry NumberNot Available
SMILES
OC1=C(Cl)C=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
InChI KeyLINPIYWFGCPVIE-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Chemical Taxonomy
DescriptionThis compound 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
  • 2-chlorophenol
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.78ALOGPS
logP3.48ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)5.99ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.45 m³·mol⁻¹ChemAxon
Polarizability16.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061728
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00053610
Chemspider ID21106172
KEGG Compound IDC07098
BioCyc IDTRICHLOROPHENOL
BiGG IDNot Available
Wikipedia Link2,4,6-Trichlorophenol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28755
Good Scents IDNot Available
References
General References
  1. Authors unspecified: 2,4,6-Trichlorophenol. Rep Carcinog. 2011;12:424-6. [PubMed:21863115 ]
  2. Huff J: Long-term toxicology and carcinogenicity of 2,4,6-trichlorophenol. Chemosphere. 2012 Oct;89(5):521-5. doi: 10.1016/j.chemosphere.2012.05.015. Epub 2012 Jun 27. [PubMed:22748215 ]
  3. Wang S, Zhang W, Yang KL, He J: Isolation and characterization of a novel Dehalobacter species strain TCP1 that reductively dechlorinates 2,4,6-trichlorophenol. Biodegradation. 2014 Apr;25(2):313-23. doi: 10.1007/s10532-013-9662-1. Epub 2013 Aug 31. [PubMed:23995979 ]
  4. Kim K, Park H, Lee JH: Urinary concentrations of trichlorophenols in the Korean adult population: results of the National Human Biomonitoring Survey 2009. Environ Sci Pollut Res Int. 2014 Feb;21(4):2479-85. doi: 10.1007/s11356-013-2180-1. [PubMed:24078273 ]