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Showing metabocard for Chlorothalonil (HMDB0250125)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:06:00 UTC
Update Date2021-09-26 23:01:23 UTC
HMDB IDHMDB0250125
Secondary Accession NumbersNone
Metabolite 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 formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Chlorothalonil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Chlorothalonil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Chlorothalonil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250125 (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
Download

3D MOL for HMDB0250125 (Chlorothalonil)

HMDB0250125
     RDKit          3D
Chlorothalonil
 14 14  0  0  0  0  0  0  0  0999 V2000
    3.7162   -0.9476   -0.2239 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6136   -0.5806   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441   -0.1187   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.2296   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2225    2.4353   -0.0247 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687    1.6235    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    3.3320    0.1667 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3557    0.6432    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    1.1654    0.2025 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820   -0.6968    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1135   -1.7079    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9482   -2.5174    0.0728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -1.0788   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -2.7811   -0.1440 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  3  0
 10 13  2  0
 13 14  1  0
 13  3  1  0
M  END
Download

3D SDF for HMDB0250125 (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>
HMDB0250125

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0250125 (Chlorothalonil)

HMDB0250125
     RDKit          3D
Chlorothalonil
 14 14  0  0  0  0  0  0  0  0999 V2000
    3.7162   -0.9476   -0.2239 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6136   -0.5806   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441   -0.1187   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.2296   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2225    2.4353   -0.0247 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687    1.6235    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    3.3320    0.1667 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3557    0.6432    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    1.1654    0.2025 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820   -0.6968    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1135   -1.7079    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9482   -2.5174    0.0728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -1.0788   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -2.7811   -0.1440 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  3  0
 10 13  2  0
 13 14  1  0
 13  3  1  0
M  END
Download

PDB for HMDB0250125 (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 HMDB0250125 (Chlorothalonil)

COMPND    HMDB0250125
HETATM    1  N1  UNL     1       3.716  -0.948  -0.224  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.614  -0.581  -0.162  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.244  -0.119  -0.072  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.951   1.230  -0.004  1.00  0.00           C  
HETATM    5 CL1  UNL     1       2.223   2.435  -0.025  1.00  0.00          CL  
HETATM    6  C4  UNL     1      -0.369   1.623   0.080  1.00  0.00           C  
HETATM    7 CL2  UNL     1      -0.751   3.332   0.167  1.00  0.00          CL  
HETATM    8  C5  UNL     1      -1.356   0.643   0.094  1.00  0.00           C  
HETATM    9 CL3  UNL     1      -3.024   1.165   0.202  1.00  0.00          CL  
HETATM   10  C6  UNL     1      -1.082  -0.697   0.028  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.114  -1.708   0.043  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.948  -2.517   0.073  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.245  -1.079  -0.057  1.00  0.00           C  
HETATM   14 CL4  UNL     1       0.651  -2.781  -0.144  1.00  0.00          CL  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5    6
CONECT    6    7    8    8
CONECT    8    9   10
CONECT   10   11   13   13
CONECT   11   12   12   12
CONECT   13   14
END
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SMILES for HMDB0250125 (Chlorothalonil)

ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl
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INCHI for HMDB0250125 (Chlorothalonil)

InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,3-DicyanotetrachlorobenzeneChEBI
2,4,5,6-Tetrachloro-3-cyanobenzonitrileChEBI
DaconilChEBI
m-TCPNChEBI
m-TetrachlorophthalonitrileChEBI
Meta-TCPNChEBI
Meta-tetrachlorophthalodinitrileChEBI
TetrachloroisophthalonitrileChEBI
TPNChEBI
BravoMeSH
HydroxychlorothalonilMeSH
Chemical FormulaC8Cl4N2
Average Molecular Weight265.911
Monoisotopic Molecular Weight263.881558838
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
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
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.71730932474
DeepCCS[M-H]-146.35930932474
DeepCCS[M-2H]-180.10830932474
DeepCCS[M+Na]+155.19630932474
AllCCS[M+H]+144.132859911
AllCCS[M+H-H2O]+140.432859911
AllCCS[M+NH4]+147.632859911
AllCCS[M+Na]+148.632859911
AllCCS[M-H]-130.432859911
AllCCS[M+Na-2H]-130.632859911
AllCCS[M+HCOO]-130.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorothalonilClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl2495.9Standard polar33892256
ChlorothalonilClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl1787.2Standard non polar33892256
ChlorothalonilClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl1815.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlorothalonil GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0090000000-d566d379b31b52559e5e2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorothalonil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-02t9-1390000000-74d812beaa5ccd60e60b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 10V, Positive-QTOFsplash10-03di-0090000000-aaee35a70f1d90febbb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 20V, Positive-QTOFsplash10-03di-0090000000-aaee35a70f1d90febbb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 40V, Positive-QTOFsplash10-03di-0090000000-aaee35a70f1d90febbb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 10V, Negative-QTOFsplash10-03di-0090000000-5d7f1c0e056f6eeed4fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 20V, Negative-QTOFsplash10-03di-0090000000-5d7f1c0e056f6eeed4fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 40V, Negative-QTOFsplash10-03di-0090000000-5d7f1c0e056f6eeed4fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 10V, Positive-QTOFsplash10-03di-0090000000-61a9942377c1376495442021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 20V, Positive-QTOFsplash10-03di-0090000000-61a9942377c1376495442021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorothalonil 40V, Positive-QTOFsplash10-03di-0090000000-61a9942377c1376495442021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13861400
KEGG Compound IDC11037
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorothalonil
METLIN IDNot Available
PubChem Compound15910
PDB IDNot Available
ChEBI ID3639
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1310611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]