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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:40:39 UTC

Update Date

2021-09-26 23:08:22 UTC

HMDB ID

HMDB0254398

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mecoprop

Description

Methylchlorophenoxypropionic acid, also known as 4-chloro-2-methylphenoxy-a-propionate or 2-(4-chloro-2-tolyloxy)propionic acid, 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. The affinity for the Ah receptor depends on the structure of the specific CDD. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. Methylchlorophenoxypropionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Methylchlorophenoxypropionic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Mecoprop, or methylchlorophenoxypropionic acid (MCPP), is a common general use herbicide found in many household weed killers and weed-and-feed type lawn fertilizers. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known human carcinogen. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. It is primarily used to control broadleaf weeds. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mecoprop is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mecoprop 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02241204062D          

 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 C   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>
HMDB0254398

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(OC1=CC=C(Cl)C=C1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)

> <INCHI_KEY>
WNTGYJSOUMFZEP-UHFFFAOYSA-N

> <FORMULA>
C10H11ClO3

> <MOLECULAR_WEIGHT>
214.646

> <EXACT_MASS>
214.039671925

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.78006669805961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-chloro-2-methylphenoxy)propanoic acid

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.9797881666666663

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.465225835748273

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901555789130794

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.94570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mecoprop

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Chloro-2-methylphenoxy)propionic acid	ChEBI
2-(4-Chloro-2-tolyloxy)propionic acid	ChEBI
2-(p-Chloro-O-tolyloxy)propionic acid	ChEBI
4-Chloro-2-methylphenoxy-alpha-propionic acid	ChEBI
Mecoprop	ChEBI
O-(4-Chloro-2-methylphenyl)lactic acid	ChEBI
2-(4-Chloro-2-methylphenoxy)propionate	Generator
2-(4-Chloro-2-tolyloxy)propionate	Generator
2-(p-Chloro-O-tolyloxy)propionate	Generator
4-Chloro-2-methylphenoxy-a-propionate	Generator
4-Chloro-2-methylphenoxy-a-propionic acid	Generator
4-Chloro-2-methylphenoxy-alpha-propionate	Generator
4-Chloro-2-methylphenoxy-α-propionate	Generator
4-Chloro-2-methylphenoxy-α-propionic acid	Generator
O-(4-Chloro-2-methylphenyl)lactate	Generator
Methylchlorophenoxypropionate	Generator
Mecoprop, potassium salt	MeSH
Mecoprop, potassium salt, (+-)-isomer	MeSH
Mecoprop, sodium salt, (+-)-isomer	MeSH
Mecoprop, (R)-isomer	MeSH
Mecoprop, ammonium salt	MeSH
2-Methyl-4-chlorophenoxypropionic acid	MeSH
Mecoprop, (+-)-isomer	MeSH
Mecoprop, (S)-isomer	MeSH
Mecoprop, sodium salt	MeSH

Chemical Formula

C₁₀H₁₁ClO₃

Average Molecular Weight

214.646

Monoisotopic Molecular Weight

214.039671925

IUPAC Name

2-(4-chloro-2-methylphenoxy)propanoic acid

Traditional Name

mecoprop

CAS Registry Number

Not Available

SMILES

CC(OC1=CC=C(Cl)C=C1C)C(O)=O

InChI Identifier

InChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)

InChI Key

WNTGYJSOUMFZEP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

2-phenoxypropionic acids

Direct Parent

2-phenoxypropionic acids

Alternative Parents

Substituents

2-phenoxypropionic acid
Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Toluene
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:75704 )
monocarboxylic acid (CHEBI:75704 )
monochlorobenzenes (CHEBI:75704 )
Phenoxy herbicides (C18742 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.87	ALOGPS
logP	2.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.95 m³·mol⁻¹	ChemAxon
Polarizability	20.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	140.236	30932474
DeepCCS	[M-H]-	136.636	30932474
DeepCCS	[M-2H]-	173.882	30932474
DeepCCS	[M+Na]+	149.42	30932474
AllCCS	[M+H]+	145.1	32859911
AllCCS	[M+H-H2O]+	141.2	32859911
AllCCS	[M+NH4]+	148.8	32859911
AllCCS	[M+Na]+	149.8	32859911
AllCCS	[M-H]-	144.1	32859911
AllCCS	[M+Na-2H]-	144.8	32859911
AllCCS	[M+HCOO]-	145.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mecoprop	CC(OC1=CC=C(Cl)C=C1C)C(O)=O	2800.4	Standard polar	33892256
Mecoprop	CC(OC1=CC=C(Cl)C=C1C)C(O)=O	1688.7	Standard non polar	33892256
Mecoprop	CC(OC1=CC=C(Cl)C=C1C)C(O)=O	1696.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mecoprop GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1900000000-ac5895b5fc793274272e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mecoprop GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mecoprop GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mecoprop GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-4910000000-7bdfa1d9086c4836e053	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 90V, Negative-QTOF	splash10-0006-0900000000-11480ccdc682acf643a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 35V, Negative-QTOF	splash10-0006-0900000000-35ac6c6fa42b085bff76	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 30V, Negative-QTOF	splash10-0006-0900000000-a5fe008b371ac3a09068	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 15V, Negative-QTOF	splash10-01ox-0940000000-d67151b96f4db9b5c8fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 35V, Negative-QTOF	splash10-0006-0900000000-7c2c26ebad0bbc389d73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 75V, Negative-QTOF	splash10-0006-0900000000-78fe325c97eeb615bb6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 35V, Negative-QTOF	splash10-0006-0900000000-d1d892cf06b30e189f20	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 90V, Negative-QTOF	splash10-0006-0900000000-f13d6ff14498342f7f7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 75V, Negative-QTOF	splash10-0006-0900000000-cc43b19d54523b6fdb91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 15V, Negative-QTOF	splash10-01ox-0940000000-1991429b9e6b1d34daf3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 30V, Negative-QTOF	splash10-0006-0900000000-bb036567f924f1bfd16f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 45V, Negative-QTOF	splash10-0006-0900000000-3ea2459793789ac2ab76	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 45V, Negative-QTOF	splash10-0006-0900000000-4075a19636afe9c55f70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mecoprop 60V, Negative-QTOF	splash10-0006-0900000000-ff229e048896cb82eea8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 10V, Positive-QTOF	splash10-014i-1980000000-8c7b5fb29aab1f034b32	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 20V, Positive-QTOF	splash10-00kf-2910000000-832e0bf62c4c2e533d5d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 40V, Positive-QTOF	splash10-01ox-3900000000-5181e68db5f5e77a3c05	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 10V, Negative-QTOF	splash10-03di-0290000000-8bd0d82fa7cbbb521f18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 20V, Negative-QTOF	splash10-01ox-0930000000-d64f57906ccd7632a322	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 40V, Negative-QTOF	splash10-052f-1900000000-32d683cd7014a51a8388	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 10V, Positive-QTOF	splash10-00kf-0920000000-3ebee7efd38e453bedba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 20V, Positive-QTOF	splash10-00kf-0900000000-11415a668ebe7ae530dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 40V, Positive-QTOF	splash10-0006-9800000000-49b96972eeb200dc85ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 10V, Negative-QTOF	splash10-0006-2920000000-143d9ac5b3dca1a57235	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mecoprop 20V, Negative-QTOF	splash10-001i-9000000000-64d108b3e48a8092bcb9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18742

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mecoprop

METLIN ID

Not Available

PubChem Compound

7153

PDB ID

Not Available

ChEBI ID

75704

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Mecoprop (HMDB0254398)

MOL for HMDB0254398 (Mecoprop)

3D MOL for HMDB0254398 (Mecoprop)

3D SDF for HMDB0254398 (Mecoprop)

3D-SDF for HMDB0254398 (Mecoprop)

PDB for HMDB0254398 (Mecoprop)

3D PDB for HMDB0254398 (Mecoprop)

SMILES for HMDB0254398 (Mecoprop)

INCHI for HMDB0254398 (Mecoprop)

Structure for HMDB0254398 (Mecoprop)

3D Structure for HMDB0254398 (Mecoprop)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra