Triphenyltin
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Basic Info
| Common Name | Triphenyltin(F04157) |
| 2D Structure | |
| Description | Triphenyltin is an organotin compound. Tin is a chemical element with the symbol Sn and atomic number 50. It is a natural component of the earth's crust and is obtained chiefly from the mineral cassiterite, where it occurs as tin dioxide. (L307, L309) |
| FRCD ID | F04157 |
| CAS Number | 668-34-8 |
| PubChem CID | 91481 |
| Formula | C18H15Sn+ |
| IUPAC Name | triphenylstannanylium |
| InChI Key | XBRCDWHXULVEFB-UHFFFAOYSA-N |
| InChI | InChI=1S/3C6H5.Sn/c3*1-2-4-6-5-3-1;/h3*1-5H;/q;;;+1 |
| Canonical SMILES | C1=CC=C(C=C1)[Sn+](C2=CC=CC=C2)C3=CC=CC=C3 |
| Isomeric SMILES | C1=CC=C(C=C1)[Sn+](C2=CC=CC=C2)C3=CC=CC=C3 |
| Synonyms |
Stannylium, triphenyl-
Triphenylstannylium
triphenylstannanylium
UNII-4QZ570621E
668-34-8
4QZ570621E
AC1Q1IRU
SnPh3(+)
AC1L3M5Y
[SnPh3](+)
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzene and substituted derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Metal aryl - Monocyclic benzene moiety - Hydrocarbon derivative - Organic salt - Organotin compound - Organometallic compound - Organic post-transition metal moeity - Organic cation - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 350.028 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 3 |
| Complexity | 202 |
| Monoisotopic Mass | 351.02 |
| Exact Mass | 351.02 |
| Formal Charge | 1 |
| Heavy Atom Count | 19 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxic effect of triphenyltin in the presence of nano zinc oxide to marine copepod Tigriopus japonicus. | Environ Pollut | 2018 Dec | 30232019 |
| Binary mixture toxicities of triphenyltin with tributyltin or copper to five marine organisms: Implications on environmental risk assessment. | Mar Pollut Bull | 2017 Nov 30 | 28242281 |
| Assessing the toxicity of triphenyltin to different life stages of the marine medaka Oryzias melastigma through a series of life-cycle based experiments. | Mar Pollut Bull | 2017 Nov 30 | 28242277 |
| Organotins in Neuronal Damage, Brain Function, and Behavior: A Short Review. | Front Endocrinol (Lausanne) | 2017 | 29358929 |
| Bioluminescent yeast assay for detection of organotin compounds. | Anal Chem | 2013 Jun 18 | 23662949 |
| Triphenyltin induced growth inhibition and antioxidative responses in the green microalga Scenedesmus quadricauda. | Ecotoxicology | 2011 Jan | 20981483 |
| Protective role of propolis against reproductive toxicity of triphenyltin in male rabbits. | Food Chem Toxicol | 2010 Jul | 20399825 |
| Impact of triphenyltin acetate in microcosms simulating floodplain lakes. II. Comparison of species sensitivity distributions between laboratory and semi-field. | Ecotoxicology | 2006 Jul | 16633738 |
| Toll-like receptor priming sensitizes macrophages to proinflammatory cytokine gene induction by deoxynivalenol and other toxicants. | Toxicol Sci | 2006 Aug | 16687389 |
| Influence of sediment quality on the responses of benthic invertebrates after treatment with the fungicide triphenyltin acetate. | Environ Toxicol Chem | 2005 May | 16110991 |
| Pressurised solvent extraction for organotin speciation in vegetable matrices. | Anal Bioanal Chem | 2005 Aug | 16007440 |
| Ecotoxicological effects at contaminated sites. | Toxicology | 2004 Dec 15 | 15464632 |
| Ecotoxicological problems associated with contaminated sites. | Toxicol Lett | 2003 Apr 11 | 12676484 |
| Organotin and Irgarol-1051 contamination in Singapore coastal waters. | Mar Pollut Bull | 2002 Jul | 12222894 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
- Gene Name:
- ADH5
- Uniprot ID:
- P11766
- Molecular Weight:
- 39723.945 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1B
- Uniprot ID:
- P00325
- Molecular Weight:
- 39854.21 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1C
- Uniprot ID:
- P00326
- Molecular Weight:
- 39867.27 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH4
- Uniprot ID:
- P08319
- Molecular Weight:
- 40221.335 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH6
- Uniprot ID:
- P28332
- Molecular Weight:
- 39088.335 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of peroxisome proliferator-activated receptor gamma, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Threonine-type endopeptidase activity
- Specific Function:
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly basic pH. The proteasome has an ATP-dependent proteolytic activity. This unit is responsible of the chymotrypsin-like activity of the proteasome and is one of the principal target of the proteasome inhibitor bortezomib. May catalyze basal processing of intracellular antigens. Plays a role in the protection against oxidative damage through the Nrf2-ARE pathway (By similarity).
- Gene Name:
- PSMB5
- Uniprot ID:
- P28074
- Molecular Weight:
- 28480.01 Da
- Mechanism of Action:
- Organotins inhibit the chymotrypsin-like activity of 20S and cellular proteasomes by binding to the beta-5 subunit. This results in apoptosis caused by downstream effects in the proteasome pathway.
References
- Shi G, Chen D, Zhai G, Chen MS, Cui QC, Zhou Q, He B, Dou QP, Jiang G: The proteasome is a molecular target of environmental toxic organotins. Environ Health Perspect. 2009 Mar;117(3):379-86. doi: 10.1289/ehp.11865. Epub 2008 Oct 23. [19337512 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function.
- Gene Name:
- RARB
- Uniprot ID:
- P10826
- Molecular Weight:
- 50488.63 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1A
- Uniprot ID:
- P07327
- Molecular Weight:
- 39858.37 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
- Gene Name:
- ADH7
- Uniprot ID:
- P40394
- Molecular Weight:
- 41480.985 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
- Gene Name:
- RARG
- Uniprot ID:
- P13631
- Molecular Weight:
- 50341.405 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]