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Showing NP-Card for chlorothalonil (NP0212972)

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Record Information
Version2.0
Created at2022-09-05 11:47:57 UTC
Updated at2022-09-05 11:47:57 UTC
NP-MRD IDNP0212972
Secondary Accession NumbersNone
Natural Product Identification
Common Namechlorothalonil
DescriptionChlorothalonil, also known as daconil or TPN, belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Chlorothalonil is possibly neutral. Chlorothalonil is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. It is used predominantly on peanuts, potatoes, and tomatoes. Cyanide metabolites are excreted in the urine. Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. chlorothalonil is found in Curcuma longa. chlorothalonil was first documented in 2000 (PMID: 11016668). Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland (PMID: 14575671) (PMID: 17482661) (PMID: 23116300) (PMID: 23866729).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0212972 (chlorothalonil)


  Mrv0541 02241205242D          

 14 14  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
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3D MOL for NP0212972 (chlorothalonil)

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3D SDF for NP0212972 (chlorothalonil)

  Mrv0541 02241205242D          

 14 14  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14

> <INCHI_KEY>
CRQQGFGUEAVUIL-UHFFFAOYSA-N

> <FORMULA>
C8Cl4N2

> <MOLECULAR_WEIGHT>
265.911

> <EXACT_MASS>
263.881558838

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.31018622648792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tetrachlorobenzene-1,3-dicarbonitrile

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.101616898

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
47.58

> <JCHEM_REFRACTIVITY>
56.72040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorothalonil

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0212972 (chlorothalonil)
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PDB for NP0212972 (chlorothalonil)
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 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.667   3.080   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    2   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0212972 (chlorothalonil)
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SMILES for NP0212972 (chlorothalonil)
ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl
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INCHI for NP0212972 (chlorothalonil)
InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
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Synonyms
ValueSource
1,3-DicyanotetrachlorobenzeneChEBI
2,4,5,6-Tetrachloro-3-cyanobenzonitrileChEBI
DaconilChEBI
m-TCPNChEBI
m-TetrachlorophthalonitrileChEBI
Meta-TCPNChEBI
Meta-tetrachlorophthalodinitrileChEBI
TetrachloroisophthalonitrileChEBI
TPNChEBI
HydroxychlorothalonilMeSH
BravoMeSH
Chemical FormulaC8Cl4N2
Average Mass265.9110 Da
Monoisotopic Mass263.88156 Da
IUPAC Nametetrachlorobenzene-1,3-dicarbonitrile
Traditional Namechlorothalonil
CAS Registry NumberNot Available
SMILES
ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl
InChI Identifier
InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
InChI KeyCRQQGFGUEAVUIL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Curcuma longaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzonitriles  
Direct ParentBenzonitriles  
Alternative Parents
Substituents
  • Benzonitrile
    • 

  • Halobenzene
    • 

  • Chlorobenzene
    • 

  • Aryl halide
    • 

  • Aryl chloride
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen 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
logP3.98ALOGPS
logP4.1ChemAxon
logS-4.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.58 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.72 m³·mol⁻¹ChemAxon
Polarizability21.31 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 IDNot Available
KEGG Compound IDC11037  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorothalonil  
METLIN IDNot Available
PubChem Compound15910  
PDB IDNot Available
ChEBI ID3639  
Good Scents IDNot Available
References
General References
  1. Boman A, Montelius J, Rissanen RL, Liden C: Sensitizing potential of chlorothalonil in the guinea pig and the mouse. Contact Dermatitis. 2000 Nov;43(5):273-9. doi:  10.1034/j.1600-0536.2000.043005273.x. [PubMed:11016668  ] 
  2. Sherrard RM, Murray-Gulde CL, Rodgers JH Jr, Shah YT: Comparative toxicity of chlorothalonil: Ceriodaphnia dubia and Pimephales promelas. Ecotoxicol Environ Saf. 2003 Nov;56(3):327-33. doi:  10.1016/s0147-6513(02)00073-8. [PubMed:14575671  ] 
  3. Hernandez-Hernandez CN, Valle-Mora J, Santiesteban-Hernandez A, Bello-Mendoza R: Comparative ecological risks of pesticides used in plantation production of papaya: application of the SYNOPS indicator. Sci Total Environ. 2007 Aug 1;381(1-3):112-25. doi:  10.1016/j.scitotenv.2007.03.014. Epub 2007 May 7. [PubMed:17482661  ] 
  4. Peruga A, Barreda M, Beltran J, Hernandez F: A robust GC-MS/MS method for the determination of chlorothalonil in fruits and vegetables. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(2):298-307.  doi: 10.1080/19440049.2012.738369. Epub 2012 Nov 1. [PubMed:23116300  ] 
  5. Yu S, Wages MR, Cobb GP, Maul JD: Effects of chlorothalonil on development and growth of amphibian embryos and larvae. Environ Pollut. 2013 Oct;181:329-34. doi: 10.1016/j.envpol.2013.06.017. Epub 2013  Jul 16. [PubMed:23866729  ] 
  6. LOTUS database [Link]