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Showing metabocard for 2,4,5-Trichlorophenoxyacetic acid (HMDB0245475)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:32:26 UTC
Update Date2021-09-26 22:53:57 UTC
HMDB IDHMDB0245475
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,4,5-Trichlorophenoxyacetic acid
Description2,4,5-Trichlorophenoxyacetic acid, also known as 2,4,5-T or esteron 245, belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring. 2,4,5-Trichlorophenoxyacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2,4,5-Trichlorophenoxyacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a small amount of articles have been published on 2,4,5-Trichlorophenoxyacetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,4,5-trichlorophenoxyacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,4,5-Trichlorophenoxyacetic acid 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 HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

  Mrv0541 02241204312D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 O   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
    3.5724    2.0625    0.0000 O   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
    0.7145   -1.2375    0.0000 Cl  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
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3D MOL for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

HMDB0245475
     RDKit          3D
2,4,5-Trichlorophenoxyacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.8857   -0.2462   -1.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -0.1468   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9314   -0.1134    0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -0.0677   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.0410    0.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.1228    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    0.1014   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629    0.1833   -0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    0.1491   -2.1779 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    0.2911    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7671    0.3937    0.5602 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491    0.3153    1.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8865    0.2321    1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.2687    3.1032 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0915    0.7626    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -0.9851   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325    0.8186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.0158   -1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906    0.4007    2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13  6  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  7 18  1  0
 12 19  1  0
M  END
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3D SDF for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

  Mrv0541 02241204312D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 O   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
    3.5724    2.0625    0.0000 O   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
    0.7145   -1.2375    0.0000 Cl  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245475

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13)

> <INCHI_KEY>
SMYMJHWAQXWPDB-UHFFFAOYSA-N

> <FORMULA>
C8H5Cl3O3

> <MOLECULAR_WEIGHT>
255.483

> <EXACT_MASS>
253.930427147

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.506000246678333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2,4,5-trichlorophenoxy)acetic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.1056918876666666

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.561490697444677

> <JCHEM_PKA_STRONGEST_BASIC>
-4.95086257187572

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
53.0202

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fortex

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

HMDB0245475
     RDKit          3D
2,4,5-Trichlorophenoxyacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.8857   -0.2462   -1.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -0.1468   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9314   -0.1134    0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -0.0677   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.0410    0.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.1228    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    0.1014   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629    0.1833   -0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    0.1491   -2.1779 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100    0.2911    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7671    0.3937    0.5602 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491    0.3153    1.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8865    0.2321    1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.2687    3.1032 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0915    0.7626    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -0.9851   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325    0.8186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.0158   -1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7906    0.4007    2.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13  6  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  7 18  1  0
 12 19  1  0
M  END
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PDB for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

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       5.335   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+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    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   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 HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

COMPND    HMDB0245475
HETATM    1  O1  UNL     1       3.886  -0.246  -1.934  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.254  -0.147  -0.850  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.931  -0.113   0.383  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.776  -0.068  -0.940  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.172   0.041   0.330  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.205   0.123   0.384  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.998   0.101  -0.759  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.363   0.183  -0.691  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -3.284   0.149  -2.178  1.00  0.00          CL  
HETATM   10  C6  UNL     1      -3.010   0.291   0.522  1.00  0.00           C  
HETATM   11 CL2  UNL     1      -4.767   0.394   0.560  1.00  0.00          CL  
HETATM   12  C7  UNL     1      -2.249   0.315   1.680  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.886   0.232   1.589  1.00  0.00           C  
HETATM   14 CL3  UNL     1       0.022   0.269   3.103  1.00  0.00          CL  
HETATM   15  H1  UNL     1       4.092   0.763   0.873  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.375  -0.985  -1.409  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.533   0.819  -1.551  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.488   0.016  -1.725  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.791   0.401   2.613  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6
CONECT    6    7    7   13
CONECT    7    8   18
CONECT    8    9   10   10
CONECT   10   11   12
CONECT   12   13   13   19
CONECT   13   14
END
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SMILES for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl
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INCHI for HMDB0245475 (2,4,5-Trichlorophenoxyacetic acid)

InChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2,4,5-Trichlorphenoxy)essigsaeureChEBI
2,4,5-TChEBI
2,4,5-TrichlorphenoxyessigsaeureChEBI
Esteron 245ChEBI
TrioxoneChEBI
2,4,5-TrichlorophenoxyacetateGenerator
Chemical FormulaC8H5Cl3O3
Average Molecular Weight255.483
Monoisotopic Molecular Weight253.930427147
IUPAC Name2-(2,4,5-trichlorophenoxy)acetic acid
Traditional Namefortex
CAS Registry NumberNot Available
SMILES
OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13)
InChI KeySMYMJHWAQXWPDB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentChlorophenoxyacetates
Alternative Parents
Substituents
  • Chlorophenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • 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
  • Organic oxide
  • Organochloride
  • Hydrocarbon derivative
  • Organohalogen compound
  • 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 ID1435
KEGG Compound IDC07100
BioCyc IDCPD-10896
BiGG IDNot Available
Wikipedia Link2,4,5-Trichlorophenoxyacetic_acid
METLIN IDNot Available
PubChem Compound1480
PDB IDNot Available
ChEBI ID27903
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 ]