2,2',3,3',6-Pentachlorobiphenyl
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Basic Info
| Common Name | 2,2',3,3',6-Pentachlorobiphenyl(F03633) |
| 2D Structure | |
| Description | 2,2',3,3',6-Pentachlorobiphenyl is one of 209 polychlorinated biphenyls (PCBs). PCBs are a group of synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. They were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate and cause harmful health effects. However, PCBs do not break down readily and are still found in the environment. (L4) |
| FRCD ID | F03633 |
| CAS Number | 52663-60-2 |
| PubChem CID | 40468 |
| Formula | C12H5Cl5 |
| IUPAC Name | 1,2,4-trichloro-3-(2,3-dichlorophenyl)benzene |
| InChI Key | QVWUJLANSDKRAH-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H5Cl5/c13-7-4-5-9(15)12(17)10(7)6-2-1-3-8(14)11(6)16/h1-5H |
| Canonical SMILES | C1=CC(=C(C(=C1)Cl)Cl)C2=C(C=CC(=C2Cl)Cl)Cl |
| Isomeric SMILES | C1=CC(=C(C(=C1)Cl)Cl)C2=C(C=CC(=C2Cl)Cl)Cl |
| Synonyms |
PCB-84
2,2',3,3',6-PENTACHLOROBIPHENYL
52663-60-2
UNII-VIF9S75RZV
1,1'-Biphenyl, 2,2',3,3',6-pentachloro-
VIF9S75RZV
2,2',3,3',6-Pentachloro-1,1'-biphenyl
AC1L23SU
PCB 84
SCHEMBL4447012
|
| Classifies |
Illegal Additives
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Chlorinated biphenyls |
| Direct Parent | Polychlorinated biphenyls |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Polychlorinated biphenyl - 1,2-dichlorobenzene - Halobenzene - Chlorobenzene - Aryl halide - Aryl chloride - Hydrocarbon derivative - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 326.422 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 1 |
| Complexity | 259 |
| Monoisotopic Mass | 323.883 |
| Exact Mass | 325.88 |
| XLogP | 6 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| 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+ | 0.9891 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8639 |
| P-glycoprotein Substrate | Non-substrate | 0.8147 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8786 |
| Non-inhibitor | 0.9683 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8266 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8869 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7864 |
| CYP450 2D6 Substrate | Non-substrate | 0.8237 |
| CYP450 3A4 Substrate | Non-substrate | 0.6835 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9474 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.7594 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9473 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8619 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9253 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8200 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9499 |
| Non-inhibitor | 0.8371 | |
| AMES Toxicity | Non AMES toxic | 0.9594 |
| Carcinogens | Non-carcinogens | 0.5226 |
| Fish Toxicity | High FHMT | 0.9937 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9996 |
| Honey Bee Toxicity | High HBT | 0.6475 |
| Biodegradation | Not ready biodegradable | 0.9727 |
| Acute Oral Toxicity | III | 0.8273 |
| Carcinogenicity (Three-class) | Non-required | 0.6630 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -7.3272 | LogS |
| Caco-2 Permeability | 2.0325 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7831 | LD50, mol/kg |
| Fish Toxicity | -0.3132 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.8338 | pIGC50, ug/L |
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:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
- Gene Name:
- DDC
- Uniprot ID:
- P20711
- Molecular Weight:
- 53925.815 Da
- Mechanism of Action:
- PCB inhibition of aromatic-L-amino-acid decarboxylase is believed to cause decreased dopamine synthesis.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp17.html
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family.
References
- Safe S, Bandiera S, Sawyer T, Robertson L, Safe L, Parkinson A, Thomas PE, Ryan DE, Reik LM, Levin W, et al.: PCBs: structure-function relationships and mechanism of action. Environ Health Perspect. 1985 May;60:47-56. [2992927 ]
- General Function:
- Tyrosine 3-monooxygenase activity
- Specific Function:
- Plays an important role in the physiology of adrenergic neurons.
- Gene Name:
- TH
- Uniprot ID:
- P07101
- Molecular Weight:
- 58599.545 Da
- Mechanism of Action:
- PCB inhibition of tyrosine 3-monooxygenase is believed to cause decreased dopamine synthesis.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp17.html
- General Function:
- Polychlorinated biphenyl binding
- Specific Function:
- Binds phosphatidylcholine, phosphatidylinositol, polychlorinated biphenyls (PCB) and weakly progesterone, potent inhibitor of phospholipase A2.
- Gene Name:
- SCGB1A1
- Uniprot ID:
- P11684
- Molecular Weight:
- 9993.6 Da
- Mechanism of Action:
- PCBs will bioaccumulate by binding to receptor proteins such as uteroglobin.
References
- Troisi GM, Haraguchi K, Kaydoo DS, Nyman M, Aguilar A, Borrell A, Siebert U, Mason CF: Bioaccumulation of polychlorinated biphenyls (PCBs) and dichlorodiphenylethane (DDE) methyl sulfones in tissues of seal and dolphin morbillivirus epizootic victims. J Toxicol Environ Health A. 2001 Jan 12;62(1):1-8. [11205532 ]
- 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 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
- Gene Name:
- SULT1E1
- Uniprot ID:
- P49888
- Molecular Weight:
- 35126.185 Da
- Mechanism of Action:
- PCBs can cause endocrine disurption by binding to estrogen sulfotransferase, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction.
References
- Aoki Y: Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters--what we have learned from Yusho disease. Environ Res. 2001 May;86(1):2-11. [11386736 ]