BIS(TRI-N-BUTYLTIN) OXIDE
General Information
| Mainterm | BIS(TRI-N-BUTYLTIN) OXIDE |
| CAS Reg.No.(or other ID) | 56-35-9 |
| Regnum |
175.105 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 16682746 |
| IUPAC Name | tributyl(tributylstannyloxy)stannane |
| InChI | InChI=1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;; |
| InChI Key | APQHKWPGGHMYKJ-UHFFFAOYSA-N |
| Canonical SMILES | CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC |
| Molecular Formula | C24H54OSn2 |
| Wikipedia | tributyltin oxide |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 596.115 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 20 |
| Complexity | 246.0 |
| CACTVS Substructure Key Fingerprint | A A A D c f B 4 I A A A A A A A A A C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G A A A A A A A C A C A A A A C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 9.2 |
| Monoisotopic Mass | 598.222 |
| Exact Mass | 596.221 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| 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 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9817 |
| Human Intestinal Absorption | HIA+ | 0.7220 |
| Caco-2 Permeability | Caco2+ | 0.5910 |
| P-glycoprotein Substrate | Non-substrate | 0.5493 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8228 |
| Non-inhibitor | 0.9393 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8628 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3881 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8389 |
| CYP450 2D6 Substrate | Non-substrate | 0.8123 |
| CYP450 3A4 Substrate | Non-substrate | 0.5918 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7731 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8525 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9241 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8340 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9593 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9348 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6039 |
| Non-inhibitor | 0.7070 | |
| AMES Toxicity | Non AMES toxic | 0.8791 |
| Carcinogens | Carcinogens | 0.8135 |
| Fish Toxicity | High FHMT | 0.6706 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9530 |
| Honey Bee Toxicity | High HBT | 0.7029 |
| Biodegradation | Not ready biodegradable | 0.8966 |
| Acute Oral Toxicity | III | 0.6945 |
| Carcinogenicity (Three-class) | Non-required | 0.5625 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2148 | LogS |
| Caco-2 Permeability | 0.9322 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0865 | LD50, mol/kg |
| Fish Toxicity | 1.2401 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2839 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral ; inhalation ; dermal |
|---|---|
| Mechanism of Toxicity | Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. |
| Metabolism | Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. |
| Toxicity Values | LD50: 7210 ug/kg (Intraperitoneal, Rat) LD50: 11 700 mg/kg (Subcutaneous, Rat) LD50: 55 mg/kg (Oral, Mouse) LD50: 6 mg/kg (Intravenous, Mouse) LD50: 900 mg/kg (Dermal, Rabbit) |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Breathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308) |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organometallic compounds |
| Class | Organo-post-transition metal compounds |
| Subclass | Organotin compounds |
| Intermediate Tree Nodes | Triorganotin compounds |
| Direct Parent | Trialkyltins |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Trialkyltin - Organic metal salt - Organic oxygen compound - Hydrocarbon derivative - Organic tin salt - Organic salt - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as trialkyltins. These are triorganotin compounds where the tin atom is linked to exactly three alkyl groups. |
From ClassyFire
Targets
- General Function:
- Thioredoxin-disulfide reductase activity
- Specific Function:
- Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enhances the transcriptional activity of estrogen receptors alpha and beta while isoform 5 enhances the transcriptional activity of the beta receptor only. Isoform 5 also mediates cell death induced by a combination of interferon-beta and retinoic acid.
- Gene Name:
- TXNRD1
- Uniprot ID:
- Q16881
- Molecular Weight:
- 70905.58 Da
References
- Bragadin M, Scutari G, Folda A, Bindoli A, Rigobello MP: Effect of metal complexes on thioredoxin reductase and the regulation of mitochondrial permeability conditions. Ann N Y Acad Sci. 2004 Dec;1030:348-54. [15659816 ]
- General Function:
- Thioredoxin-disulfide reductase activity
- Specific Function:
- Maintains thioredoxin in a reduced state. Implicated in the defenses against oxidative stress. May play a role in redox-regulated cell signaling.
- Gene Name:
- TXNRD2
- Uniprot ID:
- Q9NNW7
- Molecular Weight:
- 56506.275 Da
References
- Bragadin M, Scutari G, Folda A, Bindoli A, Rigobello MP: Effect of metal complexes on thioredoxin reductase and the regulation of mitochondrial permeability conditions. Ann N Y Acad Sci. 2004 Dec;1030:348-54. [15659816 ]
- General Function:
- Thioredoxin-disulfide reductase activity
- Specific Function:
- Displays thioredoxin reductase, glutaredoxin and glutathione reductase activities. Catalyzes disulfide bond isomerization. Promotes disulfide bond formation between GPX4 and various sperm proteins and may play a role in sperm maturation by promoting formation of sperm structural components (By similarity).
- Gene Name:
- TXNRD3
- Uniprot ID:
- Q86VQ6
- Molecular Weight:
- 70682.52 Da
References
- Bragadin M, Scutari G, Folda A, Bindoli A, Rigobello MP: Effect of metal complexes on thioredoxin reductase and the regulation of mitochondrial permeability conditions. Ann N Y Acad Sci. 2004 Dec;1030:348-54. [15659816 ]
- 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
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
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 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
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 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
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
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 ]
From T3DB