1,4-DIOXANE
General Information
| Mainterm | 1,4-DIOXANE |
| CAS Reg.No.(or other ID) | 123-91-1 |
| Regnum |
175.105 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 31275 |
| IUPAC Name | 1,4-dioxane |
| InChI | InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 |
| InChI Key | RYHBNJHYFVUHQT-UHFFFAOYSA-N |
| Canonical SMILES | C1COCCO1 |
| Molecular Formula | C4H8O2 |
| Wikipedia | dioxane |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 88.106 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 26.5 |
| CACTVS Substructure Key Fingerprint | A A A D c c B g M 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 k A A A A A A A A A A A A A A A A G g A A A A A A A A C g g A I A A A A A B 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 B A A A A A A A C 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 A A A A A = = |
| Topological Polar Surface Area | 18.5 |
| Monoisotopic Mass | 88.052 |
| Exact Mass | 88.052 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| 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
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9762 |
| Human Intestinal Absorption | HIA+ | 0.9846 |
| Caco-2 Permeability | Caco2+ | 0.6406 |
| P-glycoprotein Substrate | Non-substrate | 0.7055 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9338 |
| Non-inhibitor | 0.9807 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7580 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5943 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8964 |
| CYP450 2D6 Substrate | Non-substrate | 0.8272 |
| CYP450 3A4 Substrate | Non-substrate | 0.7651 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8674 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8987 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9587 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8661 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9820 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9459 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7094 |
| Non-inhibitor | 0.9431 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8754 |
| Fish Toxicity | Low FHMT | 0.9669 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5096 |
| Honey Bee Toxicity | High HBT | 0.5908 |
| Biodegradation | Not ready biodegradable | 0.7770 |
| Acute Oral Toxicity | III | 0.8787 |
| Carcinogenicity (Three-class) | Warning | 0.5245 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.3519 | LogS |
| Caco-2 Permeability | 1.6250 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3531 | LD50, mol/kg |
| Fish Toxicity | 3.8877 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.0830 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral ; inhalation ; dermal |
|---|---|
| Mechanism of Toxicity | Though the mechanism of toxicity of 1,4-dioxane has not yet been elucidated, it is known that its carcinogenic effects are caused by a non-genotoxic mechanism that is most likely cytotoxic in nature. |
| Metabolism | Exposure to 1,4-dioxane may occur by inhalation, ingestion, and to a lesser extent by dermal contact. 1,4-Dioxane is quickly absorbed and metabolized to beta-hydroxyethoxyacetic acid (HEAA) by mixed-function oxidase enzymes. HEAA can then be converted to 1,4-dioxane-2-one under acidic conditions. Both of these products are rapidly and extensively eliminated in the urine (>95%). Unchanged 1,4-dioxane can also be excreted in the urine and in exhaled air, but mainly after high-dose exposure. |
| Toxicity Values | LD50: 1550 mg/kg (Intravenous, Rabbit) LD50: 4350 mg/kg (Subcutaneous, Mouse) LD50: >8300 mg/kg (Dermal, Rabbit) LD50: 2100 mg/kg (Oral, Dog) LD50: 799 mg/kg (Intraperitoneal, Rat) LC50: 46 g/m3 over 2 hours (Inhalation, Rat) |
| Lethal Dose | 470 ppm for an adult human. |
| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. |
| Minimum Risk Level | None |
| Health Effects | 1,4-Dioxane for short period of time cause eye and nose irritation at low levels, and severe kidney and liver effects and possibly death at very high levels. For long-term exposure, studies in animals have shown that breathing vapors of 1,4-dioxane, swallowing liquid 1,4-dioxane or contaminated drinking water, or having skin contact with liquid 1,4-dioxane affects mainly the liver and kidneys. Studies in workers did not indicate whether 1,4-dioxane causes cancer, but animal studies suggest that it is a probable human carcinogen. (L1189) |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Dioxanes |
| Subclass | 1,4-dioxanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,4-dioxanes |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Para-dioxane - Oxacycle - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4. |
From ClassyFire
Targets
- General Function:
- Lipid binding
- Specific Function:
- Binds to membranes enriched in phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5)P2). Modifies membrane curvature and facilitates the formation of clathrin-coated invaginations (By similarity). Regulates receptor-mediated endocytosis.
- Gene Name:
- EPN1
- Uniprot ID:
- Q9Y6I3
- Molecular Weight:
- 60292.655 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- General Function:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Involved in embryogenesis and cell differentiation.
- Gene Name:
- TGFB3
- Uniprot ID:
- P10600
- Molecular Weight:
- 47327.895 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- General Function:
- Receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF13B/TACI and TNFRSF17/BCMA. TNFSF13/APRIL binds to the same 2 receptors. Together, they form a 2 ligands -2 receptors pathway involved in the stimulation of B- and T-cell function and the regulation of humoral immunity. A third B-cell specific BAFF-receptor (BAFFR/BR3) promotes the survival of mature B-cells and the B-cell response.Isoform 2 seems to inhibit isoform 1 secretion and bioactivity.Isoform 3: Acts as a transcription factor for its own parent gene, in association with NF-kappa-B p50 subunit, at least in autoimmune and proliferative B-cell diseases. The presence of Delta4BAFF is essential for soluble BAFF release by IFNG/IFN-gamma-stimulated monocytes and for B-cell survival. It can directly or indirectly regulate the differential expression of a large number of genes involved in the innate immune response and the regulation of apoptosis.
- Gene Name:
- TNFSF13B
- Uniprot ID:
- Q9Y275
- Molecular Weight:
- 31222.48 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
From T3DB