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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:37:47 UTC

Update Date

2021-09-26 23:08:19 UTC

HMDB ID

HMDB0254366

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(4-Chloro-2-methylphenoxy)acetic acid

Description

2-Methyl-4-chlorophenoxyacetic acid, also known as 2,4-mcpa or agroxone, 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. This includes 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. 2-Methyl-4-chlorophenoxyacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methyl-4-chlorophenoxyacetic acid 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. Clovers are tolerant at moderate application levels. Treatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. This compound has been identified in human blood as reported by (PMID: 31557052 ). (4-chloro-2-methylphenoxy)acetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (4-Chloro-2-methylphenoxy)acetic 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

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

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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
((4-Chloro-O-tolyl)oxy)acetic acid	ChEBI
(2-Methyl-4-chlorophenoxy)acetic acid	ChEBI
2,4-MCPA	ChEBI
2-Methyl-4-chlorphenoxyessigsaeure	ChEBI
[(4-Chloro-O-tolyl)oxy]acetic acid	ChEBI
Agroxone	ChEBI
MCP	ChEBI
MCPA	ChEBI
((4-Chloro-O-tolyl)oxy)acetate	Generator
(2-Methyl-4-chlorophenoxy)acetate	Generator
[(4-Chloro-O-tolyl)oxy]acetate	Generator
2-Methyl-4-chlorophenoxyacetate	Generator
Methoxone	MeSH
2 Methyl 4 chlorophenoxyacetic acid	MeSH

Chemical Formula

C₉H₉ClO₃

Average Molecular Weight

200.619

Monoisotopic Molecular Weight

200.024021861

IUPAC Name

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

Traditional Name

zelan

CAS Registry Number

Not Available

SMILES

CC1=CC(Cl)=CC=C1OCC(O)=O

InChI Identifier

InChI=1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)

InChI Key

WHKUVVPPKQRRBV-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Chlorophenoxyacetates

Alternative Parents

Substituents

Chlorophenoxyacetate
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

monochlorobenzenes (CHEBI:50099 )
chlorophenoxyacetic acid (CHEBI:50099 )
Phenoxy herbicides (C18528 )

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	2.41	ALOGPS
logP	2.41	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.36	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	48.45 m³·mol⁻¹	ChemAxon
Polarizability	19.21 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]+	134.942	30932474
DeepCCS	[M-H]-	131.113	30932474
DeepCCS	[M-2H]-	168.234	30932474
DeepCCS	[M+Na]+	143.774	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	144.1	32859911
AllCCS	[M+Na]+	145.2	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.0	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4-Chloro-2-methylphenoxy)acetic acid	CC1=CC(Cl)=CC=C1OCC(O)=O	2858.0	Standard polar	33892256
(4-Chloro-2-methylphenoxy)acetic acid	CC1=CC(Cl)=CC=C1OCC(O)=O	1623.3	Standard non polar	33892256
(4-Chloro-2-methylphenoxy)acetic acid	CC1=CC(Cl)=CC=C1OCC(O)=O	1689.4	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 - (4-Chloro-2-methylphenoxy)acetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5910000000-860ca41c738b41f7b504	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f96-7930000000-6ca0a096b6e50d7722b1	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 - (4-Chloro-2-methylphenoxy)acetic acid 60V, Negative-QTOF	splash10-0006-0900000000-ff229e048896cb82eea8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 90V, Negative-QTOF	splash10-0006-0900000000-17d15181eb2b419433e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 75V, Negative-QTOF	splash10-0006-0900000000-2ea18be66a01057572e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 90V, Negative-QTOF	splash10-0006-0900000000-4075a19636afe9c55f70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 15V, Negative-QTOF	splash10-0005-0900000000-e70d941bd3d16b1a9f72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 30V, Negative-QTOF	splash10-0006-0900000000-795ed8a189928639332e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 35V, Negative-QTOF	splash10-0006-0900000000-7eb0c60951b148ac7643	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 35V, Negative-QTOF	splash10-0006-0900000000-b6fd64e83a2ef8f9f587	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 90V, Negative-QTOF	splash10-0006-0900000000-f8b486493ca73907b87d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 45V, Negative-QTOF	splash10-0006-0900000000-43bf20d21e9cd16dedf6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 60V, Negative-QTOF	splash10-0006-0900000000-48b5c0927cd1bec5e6b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 75V, Negative-QTOF	splash10-0006-0900000000-18b0498fb0604b831b99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 30V, Negative-QTOF	splash10-0006-0900000000-d470f18c127833c5c28e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 15V, Negative-QTOF	splash10-0006-0900000000-7e7c62ac5d04fe45fd2d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 50V, Negative-QTOF	splash10-0002-0900000000-6b72ca1fdd5e73f53870	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 35V, Negative-QTOF	splash10-0006-0900000000-3a1ceb59eb92c79ea962	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 15V, Negative-QTOF	splash10-0005-0900000000-cab6faf69b70080c6b15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 30V, Negative-QTOF	splash10-0006-0900000000-70c39f43575e12567240	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 10V, Positive-QTOF	splash10-0udi-0190000000-adfde0044cfc6ea40a2d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 20V, Positive-QTOF	splash10-0udi-1690000000-f8cc589fb93acc1df5dd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 40V, Positive-QTOF	splash10-0006-3900000000-466950da4a977e9d5021	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 10V, Negative-QTOF	splash10-0002-0900000000-47df881008b2c5f12517	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 20V, Negative-QTOF	splash10-0002-0900000000-4bf18997df6aa7f82e4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 40V, Negative-QTOF	splash10-000i-2900000000-64c749464336695fcb87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Chloro-2-methylphenoxy)acetic acid 10V, Positive-QTOF	splash10-0udi-0390000000-cc9acefac078097ce3ba	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

C18528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MCPA

METLIN ID

Not Available

PubChem Compound

7204

PDB ID

Not Available

ChEBI ID

50099

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 (4-Chloro-2-methylphenoxy)acetic acid (HMDB0254366)

MOL for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

3D MOL for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

3D SDF for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

3D-SDF for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

PDB for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

3D PDB for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

SMILES for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

INCHI for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

Structure for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

3D Structure for HMDB0254366 ((4-Chloro-2-methylphenoxy)acetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra