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Showing NP-Card for dioxane (NP0269601)

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Record Information
Version2.0
Created at2022-09-08 15:09:32 UTC
Updated at2022-09-08 15:09:33 UTC
NP-MRD IDNP0269601
Secondary Accession NumbersNone
Natural Product Identification
Common Namedioxane
Description1,4-Dioxane, also known as dioxan-1,4 or p-dioxane, 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. 1,4-Dioxane is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,4-Dioxane is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. dioxane is found in Opuntia ficus-indica and Zingiber mioga. dioxane was first documented in 2003 (PMID: 14550759). A dioxane with oxygen atoms at positions 1 and 4 (PMID: 18044507) (PMID: 20598439).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0269601 (dioxane)


  Mrv0541 02231216512D          

  6  6  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
M  END
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3D MOL for NP0269601 (dioxane)

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3D SDF for NP0269601 (dioxane)

  Mrv0541 02231216512D          

  6  6  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1COCCO1

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

> <INCHI_KEY>
RYHBNJHYFVUHQT-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
8.97302947930751

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-dioxane

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-0.09395101666666672

> <ALOGPS_LOGS>
0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.853762716619993

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
22.087

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dioxane

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0269601 (dioxane)
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PDB for NP0269601 (dioxane)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0269601 (dioxane)
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SMILES for NP0269601 (dioxane)
C1COCCO1
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INCHI for NP0269601 (dioxane)
InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
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View in JSmol
Synonyms
ValueSource
1,4-DIETHYLENE dioxideChEBI
1,4-DioxacyclohexaneChEBI
1,4-DioxanChEBI
Di(ethylene oxide)ChEBI
Dioxan-1,4ChEBI
Dioxane-1,4ChEBI
Glycol ethylene etherChEBI
p-DioxaneChEBI
Tetrahydro-1,4-dioxinChEBI
Tetrahydro-p-dioxinChEBI
Tetrahydro-para-dioxinChEBI
DioxaneMeSH
Diethylene etherMeSH
DioxanMeSH
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
IUPAC Name1,4-dioxane
Traditional Namedioxane
CAS Registry NumberNot Available
SMILES
C1COCCO1
InChI Identifier
InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
InChI KeyRYHBNJHYFVUHQT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Opuntia ficus-indicaLOTUS Database
Zingiber miogaLOTUS Database
Chemical Taxonomy
Description 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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDioxanes  
Sub Class1,4-dioxanes  
Direct Parent1,4-dioxanes  
Alternative Parents
Substituents
  • Para-dioxane
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.23ALOGPS
logP-0.094ChemAxon
logS0.51ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.09 m³·mol⁻¹ChemAxon
Polarizability8.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB03316  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14440  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,4-Dioxane  
METLIN IDNot Available
PubChem Compound31275  
PDB IDNot Available
ChEBI ID47032  
Good Scents IDNot Available
References
General References
  1. Stickney JA, Sager SL, Clarkson JR, Smith LA, Locey BJ, Bock MJ, Hartung R, Olp SF: An updated evaluation of the carcinogenic potential of 1,4-dioxane. Regul Toxicol Pharmacol. 2003 Oct;38(2):183-95. doi:  10.1016/s0273-2300(03)00090-4. [PubMed:14550759  ] 
  2. Mahendra S, Petzold CJ, Baidoo EE, Keasling JD, Alvarez-Cohen L: Identification of the intermediates of in vivo oxidation of 1 ,4-dioxane by monooxygenase-containing bacteria. Environ Sci Technol. 2007 Nov 1;41(21):7330-6. doi: 10.1021/es0705745. [PubMed:18044507  ] 
  3. Vescovi T, Coleman HM, Amal R: The effect of pH on UV-based advanced oxidation technologies--1,4-dioxane degradation. J Hazard Mater. 2010 Oct 15;182(1-3):75-9. doi: 10.1016/j.jhazmat.2010.06.001.  Epub 2010 Jun 8. [PubMed:20598439  ] 
  4. LOTUS database [Link]