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Showing metabocard for 4-Chlorophenoxyacetic acid (HMDB0246399)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:25:19 UTC
Update Date2021-09-26 22:55:27 UTC
HMDB IDHMDB0246399
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Chlorophenoxyacetic acid
Description(4-chlorophenoxy)acetic acid, also known as 4-CPA or 4-chlorphenoxyessigsaeure, 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 (4-chlorophenoxy)acetic 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. Based on a literature review very few articles have been published on (4-chlorophenoxy)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-chlorophenoxyacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Chlorophenoxyacetic 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 HMDB0246399 (4-Chlorophenoxyacetic acid)

 
  Mrv1533006051513292D          
 
 12 12  0  0  0  0            999 V2000
   16.6451  -10.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -9.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6451  -11.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486  -12.4865    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0819   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0246399 (4-Chlorophenoxyacetic acid)

HMDB0246399
     RDKit          3D
4-Chlorophenoxyacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.1375    1.5387   -0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    0.6378   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6529   -0.6562   -0.9721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8335    0.8970   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -0.3155   -0.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.2886   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8881    0.8833    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    0.8398    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.3551    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -0.3746    0.4827 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2819   -1.5296   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -1.4944   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.4533   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925    1.2648    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098    1.6562   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440    1.8399    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633    1.7752    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049   -2.4654   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -2.4000   -0.5895 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  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
  8 17  1  0
 11 18  1  0
 12 19  1  0
M  END
Download

3D SDF for HMDB0246399 (4-Chlorophenoxyacetic acid)

 
  Mrv1533006051513292D          
 
 12 12  0  0  0  0            999 V2000
   16.6451  -10.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -9.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9336  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3601  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6451  -11.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3635   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486  -12.4865    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0819   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6486   -7.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246399

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)

> <INCHI_KEY>
SODPIMGUZLOIPE-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO3

> <MOLECULAR_WEIGHT>
186.59

> <EXACT_MASS>
186.0083718

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
17.245346095859624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-chlorophenoxy)acetic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.8976025349999996

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1395449324524694

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890346208865694

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.4106

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sure-set

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0246399 (4-Chlorophenoxyacetic acid)

HMDB0246399
     RDKit          3D
4-Chlorophenoxyacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.1375    1.5387   -0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    0.6378   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6529   -0.6562   -0.9721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8335    0.8970   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -0.3155   -0.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.2886   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8881    0.8833    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    0.8398    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.3551    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680   -0.3746    0.4827 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2819   -1.5296   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -1.4944   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.4533   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925    1.2648    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098    1.6562   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440    1.8399    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633    1.7752    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049   -2.4654   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -2.4000   -0.5895 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  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
  8 17  1  0
 11 18  1  0
 12 19  1  0
M  END
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PDB for HMDB0246399 (4-Chlorophenoxyacetic acid)

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      31.071 -18.675   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.743 -19.445   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.406 -19.445   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.077 -17.135   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.743 -20.985   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.406 -20.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.412 -16.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.071 -21.762   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.412 -14.819   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      31.077 -23.308   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0      33.753 -14.049   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      31.077 -14.049   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    8                                                       
CONECT    7    4    9                                                       
CONECT    8    5   10    6                                                  
CONECT    9    7   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0246399 (4-Chlorophenoxyacetic acid)

COMPND    HMDB0246399
HETATM    1  O1  UNL     1      -4.138   1.539  -0.676  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.260   0.638  -0.683  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.653  -0.656  -0.972  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.834   0.897  -0.397  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.122  -0.316  -0.486  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.243  -0.289  -0.250  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.888   0.883   0.060  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.248   0.840   0.283  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.922  -0.355   0.191  1.00  0.00           C  
HETATM   10 CL1  UNL     1       4.668  -0.375   0.483  1.00  0.00          CL  
HETATM   11  C7  UNL     1       2.282  -1.530  -0.119  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.935  -1.494  -0.341  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.377  -1.453  -0.386  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.692   1.265   0.660  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.410   1.656  -1.091  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.344   1.840   0.133  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.763   1.775   0.531  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.805  -2.465  -0.192  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.386  -2.400  -0.590  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6
CONECT    6    7    7   12
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   11
CONECT   11   12   12   18
CONECT   12   19
END
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SMILES for HMDB0246399 (4-Chlorophenoxyacetic acid)

OC(=O)COC1=CC=C(Cl)C=C1
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INCHI for HMDB0246399 (4-Chlorophenoxyacetic acid)

InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(p-Chlorophenoxy)acetic acidChEBI
4-ChlorophenoxyacetateChEBI
4-Chlorophenoxyacetic acidChEBI
4-ChlorphenoxyessigsaeureChEBI
4-CPAChEBI
Para-chlorophenoxyacetic acidChEBI
(p-Chlorophenoxy)acetateGenerator
Para-chlorophenoxyacetateGenerator
(4-Chlorophenoxy)acetateGenerator
4-Chlorophenoxyacetic acid, sodium saltMeSH
4-Chlorophenoxyacetic acid, ammonium saltMeSH
4-Chlorophenoxyacetic acid, potassium saltMeSH
P-Chlorophenoxyacetic acidMeSH
Chemical FormulaC8H7ClO3
Average Molecular Weight186.59
Monoisotopic Molecular Weight186.0083718
IUPAC Name2-(4-chlorophenoxy)acetic acid
Traditional Namesure-set
CAS Registry NumberNot Available
SMILES
OC(=O)COC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
InChI KeySODPIMGUZLOIPE-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
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 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 ID24438
KEGG Compound IDC07088
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Chlorophenoxyacetic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID1808
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1098451
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 ]