Basic Info

Common Name1,4-Dioxane(F03427)
2D Structure
Description

1,4-Dioxane (commonly referred to as simply ‘dioxane’) is used as a solvent in the manufacture of other chemicals and as a laboratory reagent. It is a trace contaminant of some chemicals used in cosmetics, detergents, and shampoos. (L1189)

FRCD IDF03427
CAS Number123-91-1
PubChem CID31275
FormulaC4H8O2
IUPAC Name

1,4-dioxane

InChI Key

RYHBNJHYFVUHQT-UHFFFAOYSA-N

InChI

InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2

Canonical SMILES

C1COCCO1

Isomeric SMILES

C1COCCO1

Wikipedia1,4-Dioxane
Synonyms
        
            1,4-DIOXANE
        
            Dioxane
        
            p-Dioxane
        
            123-91-1
        
            1,4-Diethylene dioxide
        
            Diethylene ether
        
            Dioxan
        
            Dioxanne
        
            1,4-Dioxacyclohexane
        
            Di(ethylene oxide)
        
Classifies
                

                  
                    Pollutant
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDioxanes
Subclass1,4-dioxanes
Intermediate Tree NodesNot available
Direct Parent1,4-dioxanes
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsPara-dioxane - Oxacycle - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteromonocyclic compound
DescriptionThis 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.

Properties

Property NameProperty Value
Molecular Weight88.106
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Complexity26.5
Monoisotopic Mass88.052
Exact Mass88.052
XLogP-0.3
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9762
Human Intestinal AbsorptionHIA+0.9846
Caco-2 PermeabilityCaco2+0.6406
P-glycoprotein SubstrateNon-substrate0.7055
P-glycoprotein InhibitorNon-inhibitor0.9338
Non-inhibitor0.9807
Renal Organic Cation TransporterNon-inhibitor0.7580
Distribution
Subcellular localizationMitochondria0.5943
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8964
CYP450 2D6 SubstrateNon-substrate0.8272
CYP450 3A4 SubstrateNon-substrate0.7651
CYP450 1A2 InhibitorNon-inhibitor0.8674
CYP450 2C9 InhibitorNon-inhibitor0.8987
CYP450 2D6 InhibitorNon-inhibitor0.9587
CYP450 2C19 InhibitorNon-inhibitor0.8661
CYP450 3A4 InhibitorNon-inhibitor0.9820
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9459
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7094
Non-inhibitor0.9431
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8754
Fish ToxicityLow FHMT0.9669
Tetrahymena Pyriformis ToxicityHigh TPT0.5096
Honey Bee ToxicityHigh HBT0.5908
BiodegradationNot ready biodegradable0.7770
Acute Oral ToxicityIII0.8787
Carcinogenicity (Three-class)Warning0.5245

Model Value Unit
Absorption
Aqueous solubility-0.3519LogS
Caco-2 Permeability1.6250LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.3531LD50, mol/kg
Fish Toxicity3.8877pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.0830pIGC50, ug/L

References

TitleJournalDatePubmed ID
Delignification and detoxification of peanut shell bio-waste using an extremely halophilic laccase from an Aquisalibacillus elongatus isolate.Extremophiles2017 Nov28871494
Structural basis for C-ribosylation in the alnumycin A biosynthetic pathway.Proc Natl Acad Sci U S A2013 Jan 2223297194
Biosynthetic pathway toward carbohydrate-like moieties of alnumycins containsunusual steps for C-C bond formation and cleavage.Proc Natl Acad Sci U S A2012 Apr 1722474343
Alkylating potential of potassium sorbate.J Agric Food Chem2005 Dec 2816366722
Influence of nucleic acids and polysaccharides on phosphotransferase activity of preparations of secretory immunoglobulin A from human milk.Biochemistry (Mosc)2000 Feb10713554
Liquid chromatographic determination of 2-chloro-4-nitroaniline, 2-naphthol, and 2,4-dinitroaniline in D&C red no. 36.J AOAC Int1993 Mar-Apr8471855
2,3,7,8-Tetrachlorodibenzo-p-dioxin increases reliance on fats as a fuel source independently of diet: evidence that diminished carbohydrate supply contributes to dioxin lethality.Biochem Biophys Res Commun1991 Feb 141996990
[Evaluation of toxic effects on yusho causal substances by chick embryo hepatic microsomal enzymes activities].Fukuoka Igaku Zasshi1989 May2501189
Sources of uncertainty in pharmacokinetic prediction.J Anim Sci1983 Jan6337985

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
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
  1. 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 ]