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Showing metabocard for 4-Hydroxychlorothalonil (HMDB0240624)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2020-02-04 17:24:10 UTC
Update Date2022-03-07 03:18:20 UTC
HMDB IDHMDB0240624
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxychlorothalonil
Description4-Hydroxychlorothalonil (SDS 3701) is a metabolite of the widely used fungicide chlorothalonil which is used to manage fungal diseases affecting agricultural crops around the world (PMID: 31265862 ). 4-Hydroxychlorothalonil was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240624 (4-Hydroxychlorothalonil)

  Mrv1652302042018012D          

 14 14  0  0  0  0            999 V2000
    0.4019    2.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124    2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020    1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124    3.3464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7414    2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415    0.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.0464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    2.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    2.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    2.1090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  3  8  1  0  0  0  0
  2  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  4  9  1  0  0  0  0
  1 12  1  0  0  0  0
 12 14  3  0  0  0  0
  8 13  3  0  0  0  0
M  END
Download

3D MOL for HMDB0240624 (4-Hydroxychlorothalonil)

HMDB0240624
     RDKit          3D
4-Hydroxychlorothalonil
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.4387   -2.7808    0.2101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.8819    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.7933    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.5076    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765    0.8229    0.2784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.5760    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    3.2244    0.1429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    1.2846   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1939    2.5881   -0.1849 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4317   -0.0211   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -0.2838   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -0.4878   -0.4314 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -1.0795   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -2.7282   -0.1589 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263    0.0528    0.3334 H   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
  5 15  1  0
M  END
Download

3D SDF for HMDB0240624 (4-Hydroxychlorothalonil)

  Mrv1652302042018012D          

 14 14  0  0  0  0            999 V2000
    0.4019    2.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124    2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020    1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124    3.3464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7414    2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415    0.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.0464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    2.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    2.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    2.1090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  3  8  1  0  0  0  0
  2  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  4  9  1  0  0  0  0
  1 12  1  0  0  0  0
 12 14  3  0  0  0  0
  8 13  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240624

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8HCl3N2O/c9-5-3(1-12)6(10)7(11)8(14)4(5)2-13/h14H

> <INCHI_KEY>
MDQKYGOECVSPIW-UHFFFAOYSA-N

> <FORMULA>
C8HCl3N2O

> <MOLECULAR_WEIGHT>
247.46

> <EXACT_MASS>
245.9154458

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
20.073787417986253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,5-trichloro-6-hydroxybenzene-1,3-dicarbonitrile

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
3.1940068999999998

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.015305442326652

> <JCHEM_PKA_STRONGEST_BASIC>
-8.86967416187641

> <JCHEM_POLAR_SURFACE_AREA>
67.81

> <JCHEM_REFRACTIVITY>
53.89650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trichloro-6-hydroxybenzene-1,3-dicarbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0240624 (4-Hydroxychlorothalonil)

HMDB0240624
     RDKit          3D
4-Hydroxychlorothalonil
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.4387   -2.7808    0.2101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.8819    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.7933    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.5076    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765    0.8229    0.2784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.5760    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    3.2244    0.1429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    1.2846   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1939    2.5881   -0.1849 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4317   -0.0211   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -0.2838   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -0.4878   -0.4314 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -1.0795   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -2.7282   -0.1589 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263    0.0528    0.3334 H   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
  5 15  1  0
M  END
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PDB for HMDB0240624 (4-Hydroxychlorothalonil)

HEADER    PROTEIN                                 04-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-20         0                                  
HETATM    1  C   UNK     0       0.750   3.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.583   4.707   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.917   3.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.917   2.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.583   1.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.750   2.397   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -0.583   6.247   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -3.251   4.707   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.251   1.627   0.000  0.00  0.00           O+0
HETATM   10 Cl   UNK     0      -0.583   0.087   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       2.084   1.627   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       2.084   4.707   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.584   3.937   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.418   3.937   0.000  0.00  0.00           N+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1   11                                                  
CONECT    7    2                                                            
CONECT    8    3   13                                                       
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    1   14                                                       
CONECT   13    8                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0240624 (4-Hydroxychlorothalonil)

COMPND    HMDB0240624
HETATM    1  N1  UNL     1      -2.439  -2.781   0.210  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.706  -1.882   0.147  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.787  -0.793   0.070  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.215   0.508   0.134  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.577   0.823   0.278  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.317   1.576   0.058  1.00  0.00           C  
HETATM    7 CL1  UNL     1      -0.901   3.224   0.143  1.00  0.00          CL  
HETATM    8  C5  UNL     1       1.012   1.285  -0.083  1.00  0.00           C  
HETATM    9 CL2  UNL     1       2.194   2.588  -0.185  1.00  0.00          CL  
HETATM   10  C6  UNL     1       1.432  -0.021  -0.147  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.847  -0.284  -0.296  1.00  0.00           C  
HETATM   12  N2  UNL     1       3.982  -0.488  -0.431  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.552  -1.080  -0.072  1.00  0.00           C  
HETATM   14 CL3  UNL     1       1.149  -2.728  -0.159  1.00  0.00          CL  
HETATM   15  H1  UNL     1      -3.226   0.053   0.333  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5    6
CONECT    5   15
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 HMDB0240624 (4-Hydroxychlorothalonil)

OC1=C(C#N)C(Cl)=C(C#N)C(Cl)=C1Cl
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INCHI for HMDB0240624 (4-Hydroxychlorothalonil)

InChI=1S/C8HCl3N2O/c9-5-3(1-12)6(10)7(11)8(14)4(5)2-13/h14H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Hydroxy-2,5,6-trichloro-1,3-benzenedicarbonitrileChEBI
4-Hydroxy-2,5,6-trichloroisophthalonitrileChEBI
BravoHMDB
HydroxychlorothalonilHMDB
TetrachloroisophthalonitrileHMDB
ChlorothalonilHMDB
DaconilHMDB
1,3-Dicyano-4-hydroxy-2,5,6-trichlorobenzeneHMDB
2,4,5-Trichloro-6-hydroxy-1,3-benzenedicarbonitrileHMDB
2,4,5-Trichloro-6-hydroxyisophthalonitrileHMDB
2,5,6-Trichloro-4-hydroxy-1,3-benzenedicarbonitrileHMDB
SDS 3701HMDB
4-HydroxychlorothalonilHMDB
Chemical FormulaC8HCl3N2O
Average Molecular Weight247.46
Monoisotopic Molecular Weight245.9154458
IUPAC Name2,4,5-trichloro-6-hydroxybenzene-1,3-dicarbonitrile
Traditional Name2,4,5-trichloro-6-hydroxybenzene-1,3-dicarbonitrile
CAS Registry Number28343-61-5
SMILES
OC1=C(C#N)C(Cl)=C(C#N)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C8HCl3N2O/c9-5-3(1-12)6(10)7(11)8(14)4(5)2-13/h14H
InChI KeyMDQKYGOECVSPIW-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
  • 3-halophenol
  • 2-halophenol
  • 3-chlorophenol
  • 2-chlorophenol
  • Chlorobenzene
  • Phenol
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carbonitrile
  • Nitrile
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 ID31530
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound34217
PDB IDNot Available
ChEBI ID133542
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]
  2. Lin H, Zhao S, Fan X, Ma Y, Wu X, Su Y, Hu J: Residue behavior and dietary risk assessment of chlorothalonil and its metabolite SDS-3701 in water spinach to propose maximum residue limit (MRL). Regul Toxicol Pharmacol. 2019 Oct;107:104416. doi: 10.1016/j.yrtph.2019.104416. Epub 2019 Jun 29. [PubMed:31265862 ]