2,4-Dichlorophenol
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Basic Info
| Common Name | 2,4-Dichlorophenol(F03426) |
| 2D Structure | |
| Description | 2,4-Dichlorophenol is a chlorinated organic chemical due to environmental exposure, that can be detected in breast milk. The free species of phenols and chlorinated organic appear to be most prevalent in milk (A11269). |
| FRCD ID | F03426 |
| CAS Number | 120-83-2 |
| PubChem CID | 8449 |
| Formula | C6H4Cl2O |
| IUPAC Name | 2,4-dichlorophenol |
| InChI Key | HFZWRUODUSTPEG-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H |
| Canonical SMILES | C1=CC(=C(C=C1Cl)Cl)O |
| Isomeric SMILES | C1=CC(=C(C=C1Cl)Cl)O |
| Wikipedia | 2,4-Dichlorophenol |
| Synonyms |
RCRA waste number U081
2,4-Dichlorohydroxybenzene
2,4-DICHLOROPHENOL
120-83-2
Phenol, 2,4-dichloro-
4,6-Dichlorophenol
2,4-DCP
2,4-dichloro-Phenol
1-Hydroxy-2,4-dichlorobenzene
NCI-C55345
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Halobenzenes |
| Intermediate Tree Nodes | Chlorobenzenes |
| Direct Parent | Dichlorobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 4-chlorophenol - 2-chlorophenol - 2-halophenol - 4-halophenol - 1,3-dichlorobenzene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aryl halide - Aryl chloride - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 162.997 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 97.1 |
| Monoisotopic Mass | 161.964 |
| Exact Mass | 161.964 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9643 |
| Human Intestinal Absorption | HIA+ | 0.9932 |
| Caco-2 Permeability | Caco2+ | 0.8943 |
| P-glycoprotein Substrate | Non-substrate | 0.8164 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9782 |
| Non-inhibitor | 0.9941 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8694 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8731 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7834 |
| CYP450 2D6 Substrate | Non-substrate | 0.8320 |
| CYP450 3A4 Substrate | Non-substrate | 0.6716 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8447 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6560 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9307 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5210 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8866 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6737 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8043 |
| Non-inhibitor | 0.9426 | |
| AMES Toxicity | Non AMES toxic | 0.9306 |
| Carcinogens | Non-carcinogens | 0.7562 |
| Fish Toxicity | High FHMT | 0.9126 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9877 |
| Honey Bee Toxicity | High HBT | 0.7919 |
| Biodegradation | Not ready biodegradable | 0.8276 |
| Acute Oral Toxicity | III | 0.8688 |
| Carcinogenicity (Three-class) | Non-required | 0.6275 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2778 | LogS |
| Caco-2 Permeability | 1.8233 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4130 | LD50, mol/kg |
| Fish Toxicity | 0.5640 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.5348 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Cytochrome P450-mediated metabolism of triclosan attenuates its cytotoxicity in hepatic cells. | Arch Toxicol | 2017 Jun | 27896399 |
| Production of a toxic metabolite in 2,4-D-resistant GM crop plants. | 3 Biotech | 2016 Jun | 28330152 |
| Uncaria tomentosa extracts protect human erythrocyte catalase against damage induced by 2,4-D-Na and its metabolites. | Food Chem Toxicol | 2012 Jun | 22426356 |
| Protective activity of the Uncaria tomentosa extracts on human erythrocytes in oxidative stress induced by 2,4-dichlorophenol (2,4-DCP) and catechol. | Food Chem Toxicol | 2011 Sep | 21712061 |
| Scale up of 2,4-dichlorophenol removal from aqueous solutions using Brassica napus hairy roots. | J Hazard Mater | 2011 Jan 15 | 20951495 |
| Metabolic fate of [14C] chlorophenols in radish (Raphanus sativus), lettuce (Lactuca sativa), and spinach (Spinacia oleracea). | J Agric Food Chem | 2008 Sep 24 | 18763782 |
| Automated on-line column-switching HPLC-MS/MS method with peak focusing formeasuring parabens, triclosan, and other environmental phenols in human milk. | Anal Chim Acta | 2008 Aug 1 | 18602546 |
| Plastic components affect the activation of the aryl hydrocarbon and the androgenreceptor. | Toxicology | 2008 Apr 18 | 18294747 |
| Metabolic fate of [(14)C]-2,4-dichlorophenol in tobacco cell suspension cultures. | Environ Toxicol Chem | 2007 Nov | 17941740 |
| Suitability of the OCDE tests to estimate contamination with 2,4-dichlorophenolof soils from Galicia (NW Spain). | Sci Total Environ | 2007 May 25 | 17306860 |
| Estimating pesticide dose from urinary pesticide concentration data by creatininecorrection in the Third National Health and Nutrition Examination Survey(NHANES-III). | J Expo Anal Environ Epidemiol | 2004 Nov | 15367927 |
| Retention and extractability of phenol, cresol, and dichlorophenol exposed to twosurface soils in the presence of horseradish peroxidase enzyme. | J Agric Food Chem | 2003 Jan 1 | 12502405 |
| Purification and Properties of an S-Adenosylmethionine: 2,4-Disubstituted Phenol O-Methyltransferase from Phanerochaete chrysosporium. | Appl Environ Microbiol | 1993 Mar | 16348886 |
| Supercritical carbon dioxide extraction of 2,4-dichlorophenol from food croptissues. | Anal Chem | 1992 Apr 15 | 1621998 |
Targets
- 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
- Mechanism of Action:
- 2,4-Dichlorophenol binds to androgen receptor. It inhibits 5a-dihydroxytestosterone's binding to androgen recpetor and also exhibits the synergistic androgenic activities.
References
- Kim HJ, Park YI, Dong MS: Effects of 2,4-D and DCP on the DHT-induced androgenic action in human prostate cancer cells. Toxicol Sci. 2005 Nov;88(1):52-9. Epub 2005 Aug 17. [16107550 ]
- 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
- Han DH, Denison MS, Tachibana H, Yamada K: Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci Biotechnol Biochem. 2002 Jul;66(7):1479-87. [12224631 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Transcriptionally controlled transcription factor. Binds to DNA sites required for the transcription of alpha 1-antitrypsin, apolipoprotein CIII, transthyretin genes and HNF1-alpha. May be essential for development of the liver, kidney and intestine.
- Gene Name:
- HNF4A
- Uniprot ID:
- P41235
- Molecular Weight:
- 52784.205 Da
References
- 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 ]