4-(4-Chloro-2-methylphenoxy)butanoic acid (T3D0805)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-06-02 22:28:28 UTC
Update Date2014-12-24 20:22:51 UTC
Accession NumberT3D0805
Identification
Common Name4-(4-Chloro-2-methylphenoxy)butanoic acid
ClassSmall Molecule
Description4-(4-Chloro-2-methylphenoxy)butanoic acid (MCPB, 2,4-MCPB) is a phenoxybutyric herbicide. In the United States it is registered for use on pea crops before flowering, for post-emergence control of broadleaf annual and perennial weeds including Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, and morning glory. It has low to moderate acute toxicity, with kidney and liver effects as the main hazard concerns.
Compound Type
  • Aromatic Hydrocarbon
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(2-Methyl-4-chlorophenoxy)butyric acid
(4-chloro-2-Methylphenoxy)butyric acid
(4-Chloro-o-tolyl)oxy]butyric acid
(4-chloro-O-Tolyloxy)butyric acid
2,4-MCPB
2-Methyl-4-chlorophenoxy gamma-butyric acid
2-Methyl-4-chlorophenoxybutyric acid
2M 4KhM
4-((4-chloro-O-Tolyl)oxy)butyric acid
4-(2-Methyl-4-chlorophenoxy)butyric acid
4-(4-Chloro-2-methylphenoxy)butanoate
4-(4-chloro-2-Methylphenoxy)butanoate
4-(4-chloro-2-Methylphenoxy)butanoic acid
4-(4-Chloro-2-methylphenoxy)butyric acid
4-(4-Chloro-o-tolyloxy)butyric acid
4-(MCB)
4-[(4-Chloro-o-tolyl)oxy]butyric acid
4MCPB
Belmac straight
Bexane
Bexone
Can-trol
Caswell No. 558
Fisons 18-15, MCPB
gamma-(2-Methyl-4-chlorophenoxy)butyric acid
gamma-(4-chloro-2-Methylphenoxy)butyric acid
gamma-MCPB
Gamma-MCPB
Gamma.-(2-methyl-4-chlorophenoxy)butyric acid
Gamma.-(4-chloro-2-methylphenoxy)butyric acid
gamma.-MCPB
Legumex
MCP-butyric
MCPB
PDQ
Thistrol
Thitrol
Trifolex
Tritrol
Tropotox
Trotox
U46 MCPB
{4-[(4-chloro-O-tolyl)oxy]butyric} acid
Chemical FormulaC11H13ClO3
Average Molecular Mass228.672 g/mol
Monoisotopic Mass228.055 g/mol
CAS Registry Number94-81-5
IUPAC Name4-(4-chloro-2-methylphenoxy)butanoic acid
Traditional NameMCPB
SMILESCC1=CC(Cl)=CC=C1OCCCC(O)=O
InChI IdentifierInChI=1S/C11H13ClO3/c1-8-7-9(12)4-5-10(8)15-6-2-3-11(13)14/h4-5,7H,2-3,6H2,1H3,(H,13,14)
InChI KeyInChIKey=LLWADFLAOKUBDR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Toluene
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point100°C
Boiling PointNot Available
Solubility0.048 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.75ALOGPS
logP2.94ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.91 m³·mol⁻¹ChemAxon
Polarizability23.4 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1290000000-07adf725c109c3738f4c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-4920000000-0229ca65a4b564a69ef02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-70b0cefa0395926124c12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0690000000-2401b738a16f960b16222016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0920000000-9ce30369fdc1f5e72b892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-de071d4aa7c25fd26abf2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-0d3b43ce51d5a4040c142014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMCPB is a phenoxy herbicide produced as a sodium salt and an acid. MCPB is registered for use on pea crops before flowering, for post-emergence control of broadleaf annual and perennial weeds including Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, and morning glory. (2)
Minimum Risk LevelNot Available
Health EffectsKidney and liver effects are the most prevalent hazard concerns for MCPB (2).
SymptomsNot Available
TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID7207
ChEMBL IDNot Available
ChemSpider ID6938
KEGG IDC18529
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC008418
Stitch ID4-(4-Chloro-2-methylphenoxy)butanoic acid
PDB IDNot Available
ACToR ID6482
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. US Environmental Protection Agency (2009). Recognition and Management of Pesticide Poisonings. [Link]
  2. EPA Fact Sheet on MCPB RED [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
Target Details
2. Estrogen receptor beta
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
Target Details
3. Androgen receptor
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.00 uMTox21_AR_LUC_MDAKB2_AgonistTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]