2,4,5-Trichlorophenol
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Basic Info
| Common Name | 2,4,5-Trichlorophenol(F03437) |
| 2D Structure | |
| Description | 2,4,5-Trichlorophenol is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. The chemical 2,4,5-trichlorophenol serves as a raw material for making the herbicides Silvex and 2,4,5-T (2,4,5-trichlorophenoxyacetic acid) (L159). |
| FRCD ID | F03437 |
| CAS Number | 95-95-4 |
| PubChem CID | 7271 |
| Formula | C6H3Cl3O |
| IUPAC Name | 2,4,5-trichlorophenol |
| InChI Key | LHJGJYXLEPZJPM-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H3Cl3O/c7-3-1-5(9)6(10)2-4(3)8/h1-2,10H |
| Canonical SMILES | C1=C(C(=CC(=C1Cl)Cl)Cl)O |
| Isomeric SMILES | C1=C(C(=CC(=C1Cl)Cl)Cl)O |
| Synonyms |
RCRA waste number U230
2,4,5-TRICHLOROPHENOL
95-95-4
Dowicide 2
Collunosol
Preventol I
Phenol, 2,4,5-trichloro-
2,4,5-TCP
2,4,5-Trichloro phenol
2,4,5-Trichloro-phenol
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Halophenols |
| Intermediate Tree Nodes | Chlorophenols |
| Direct Parent | P-chlorophenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 4-chlorophenol - 2-chlorophenol - 3-chlorophenol - 1-hydroxy-2-unsubstituted benzenoid - Halobenzene - Chlorobenzene - Monocyclic benzene moiety - 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 p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 197.439 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 120 |
| Monoisotopic Mass | 195.925 |
| Exact Mass | 195.925 |
| XLogP | 3.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| 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 |
|---|---|---|---|
| Metabolic fate of [14C] chlorophenols in radish (Raphanus sativus), lettuce (Lactuca sativa), and spinach (Spinacia oleracea). | J Agric Food Chem | 2008 Sep 24 | 18763782 |
| Functional importance of the family 1 glucosyltransferase UGT72B1 in the metabolism of xenobiotics in Arabidopsis thaliana. | Plant J | 2005 May | 15860014 |
Targets
- 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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- 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 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
- Mechanism of Action:
- 2,4,6-trichlorophenol (2,4,6-TCP) has been identified to hemolyze washed human erythrocytes and inhibit acetylcholinesterase (AchE) activities in the erythrocyte membrane .
References
- Matsumura H, Matsuoka M, Igisu H, Ikeda M: Cooperative inhibition of acetylcholinesterase activities by hexachlorophene in human erythrocytes. Arch Toxicol. 1997;71(3):151-6. [9049051 ]
- General Function:
- Leukotriene-b4 20-monooxygenase activity
- Specific Function:
- Catalyzes leukotriene B4 omega-hydroxylation and arachidonic acid omega-hydroxylation but with an activity much lower than that of CYP4F2. Catalyzes the hydroxylation of the antihistamine ebastine.
- Gene Name:
- CYP4F12
- Uniprot ID:
- Q9HCS2
- Molecular Weight:
- 60269.165 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 ]
- 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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 ]
- 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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- 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 ]