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Showing metabocard for Dichlorprop (HMDB0251202)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:31:55 UTC
Update Date2021-09-26 23:03:04 UTC
HMDB IDHMDB0251202
Secondary Accession NumbersNone
Metabolite Identification
Common NameDichlorprop
DescriptionDichlorprop belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid. Dichlorprop is an extremely weak basic (essentially neutral) compound (based on its pKa). Dichlorprop is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. The affinity for the Ah receptor depends on the structure of the specific CDD. In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. The EPA classifies the R-isomer as “Not Likely to be Carcinogenic to Humans.”(L369) Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dichlorprop is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dichlorprop 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 HMDB0251202 (Dichlorprop)

  Mrv0541 02241204592D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   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
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
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3D MOL for HMDB0251202 (Dichlorprop)

HMDB0251202
     RDKit          3D
Dichlorprop
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.2022   -1.4072    0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -0.4593   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    0.2842    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    0.2410    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1768   -0.5930   -0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373   -0.5944   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558    0.2702   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    0.2812   -0.9926 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    1.1013    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    1.1151    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165    2.1815    1.9594 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    0.3951   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -0.1402   -1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    1.7540   -0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -0.9219    1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -1.5699    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -2.3676    0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316   -1.1501   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -1.2759   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112   -1.2473   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    1.7885    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    2.3146    0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 10  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  5 19  1  0
  6 20  1  0
  9 21  1  0
 14 22  1  0
M  END
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3D SDF for HMDB0251202 (Dichlorprop)

  Mrv0541 02241204592D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   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
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251202

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)

> <INCHI_KEY>
MZHCENGPTKEIGP-UHFFFAOYSA-N

> <FORMULA>
C9H8Cl2O3

> <MOLECULAR_WEIGHT>
235.064

> <EXACT_MASS>
233.985049536

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.91219110976758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dichlorophenoxy)propanoic acid

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.070411453666666

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.948297737340261

> <JCHEM_PKA_STRONGEST_BASIC>
-4.957957763014637

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.70930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+,-)-dichlorprop

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0251202 (Dichlorprop)

HMDB0251202
     RDKit          3D
Dichlorprop
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.2022   -1.4072    0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -0.4593   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    0.2842    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    0.2410    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1768   -0.5930   -0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373   -0.5944   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558    0.2702   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    0.2812   -0.9926 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    1.1013    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    1.1151    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165    2.1815    1.9594 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    0.3951   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -0.1402   -1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    1.7540   -0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -0.9219    1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -1.5699    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -2.3676    0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316   -1.1501   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -1.2759   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112   -1.2473   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    1.7885    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    2.3146    0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 10  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  5 19  1  0
  6 20  1  0
  9 21  1  0
 14 22  1  0
M  END
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PDB for HMDB0251202 (Dichlorprop)

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  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0251202 (Dichlorprop)

COMPND    HMDB0251202
HETATM    1  C1  UNL     1      -2.202  -1.407   0.966  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.682  -0.459  -0.125  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.636   0.284   0.386  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.680   0.241   0.024  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.177  -0.593  -0.953  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.537  -0.594  -1.282  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.356   0.270  -0.592  1.00  0.00           C  
HETATM    8 CL1  UNL     1       5.062   0.281  -0.993  1.00  0.00          CL  
HETATM    9  C7  UNL     1       2.859   1.101   0.381  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.528   1.115   0.717  1.00  0.00           C  
HETATM   11 CL2  UNL     1       0.917   2.181   1.959  1.00  0.00          CL  
HETATM   12  C9  UNL     1      -2.800   0.395  -0.621  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.815  -0.140  -1.110  1.00  0.00           O  
HETATM   14  O3  UNL     1      -2.701   1.754  -0.533  1.00  0.00           O  
HETATM   15  H1  UNL     1      -2.115  -0.922   1.970  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.271  -1.570   0.742  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.656  -2.368   0.952  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.332  -1.150  -0.919  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.552  -1.276  -1.503  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.911  -1.247  -2.043  1.00  0.00           H  
HETATM   21  H7  UNL     1       3.514   1.788   0.929  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.885   2.315   0.280  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   12   18
CONECT    3    4
CONECT    4    5    5   10
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8    9
CONECT    9   10   10   21
CONECT   10   11
CONECT   12   13   13   14
CONECT   14   22
END
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SMILES for HMDB0251202 (Dichlorprop)

CC(OC1=CC=C(Cl)C=C1Cl)C(O)=O
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INCHI for HMDB0251202 (Dichlorprop)

InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(2,4-Dichlorophenoxy)propionic acidChEBI
2-(2,4-Dichlorophenoxy)propionateGenerator
2,4-DP CPDMeSH
DichloropropMeSH
Dichlorprop, (R)-isomerMeSH
Dichlorprop, (S)-isomerMeSH
2-Methyl-2-(2',4'-dichlorophenoxy)acetic acidMeSH
Dichlorprop, sodium saltMeSH
2-(2,4-Dichlorophenoxy)propanoic acidMeSH
Dichlorprop, (+,-)-isomerMeSH
Dichlorprop, potassium saltMeSH
Chemical FormulaC9H8Cl2O3
Average Molecular Weight235.064
Monoisotopic Molecular Weight233.985049536
IUPAC Name2-(2,4-dichlorophenoxy)propanoic acid
Traditional Name(+,-)-dichlorprop
CAS Registry NumberNot Available
SMILES
CC(OC1=CC=C(Cl)C=C1Cl)C(O)=O
InChI Identifier
InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)
InChI KeyMZHCENGPTKEIGP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub Class2-phenoxypropionic acids
Direct Parent2-phenoxypropionic acids
Alternative Parents
Substituents
  • 2-phenoxypropionic acid
  • Phenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • 1,3-dichlorobenzene
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organochloride
  • Organic oxide
  • Organohalogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
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 IDNot Available
KEGG Compound IDC11020
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDichlorprop
METLIN IDNot Available
PubChem Compound8427
PDB IDNot Available
ChEBI ID75370
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. 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 ]