oxolane (CHEBI:26911)

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ChEBI Name	oxolane

ChEBI ID	CHEBI:26911

Definition	A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000001530031

Download	Molfile XML SDF

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Wikipedia	License
Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants. Although it produces thousands of intoxications annually and several deaths, it has shown efficacy for the treatment of cancer-related pain in phase II and III clinical trials. Tetrodotoxin is a sodium channel blocker. It inhibits the firing of action potentials in neurons by binding to the voltage-gated sodium channels in nerve cell membranes and blocking the passage of sodium ions (responsible for the rising phase of an action potential) into the neuron. This prevents the nervous system from carrying messages and thus muscles from contracting in response to nervous stimulation. Its mechanism of action – selective blocking of the sodium channel – was shown definitively in 1964 by Toshio Narahashi and John W. Moore at Duke University, using the sucrose gap voltage clamp technique.
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Formula

C4H8O

Net Charge

Average Mass

72.10570

Monoisotopic Mass

72.05751

InChI

InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2

InChIKey

WYURNTSHIVDZCO-UHFFFAOYSA-N

SMILES

C1CCOC1

Roles Classification
Chemical Role(s):	polar aprotic solvent A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.

Application(s):	polar aprotic solvent A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.

ChEBI Ontology
Outgoing	oxolane (CHEBI:26911) has role polar aprotic solvent (CHEBI:48358) oxolane (CHEBI:26911) is a cyclic ether (CHEBI:37407) oxolane (CHEBI:26911) is a oxolanes (CHEBI:26912) oxolane (CHEBI:26911) is a saturated organic heteromonocyclic parent (CHEBI:36389) oxolane (CHEBI:26911) is a volatile organic compound (CHEBI:134179)

Incoming	oxolan-3-one (CHEBI:166530) has functional parent oxolane (CHEBI:26911) 2-(dichloromethyl)tetrahydrofuran (CHEBI:87308) has parent hydride oxolane (CHEBI:26911) 10-hydroxy-pre-flavunoidine (CHEBI:195495) is a oxolane (CHEBI:26911) 2,6,9-trimethyl-13-oxatetracyclo[6.3.1.1^6,9.0^1,5]tridecane (CHEBI:194089) is a oxolane (CHEBI:26911) flavunoidine(2+) (CHEBI:194091) is a oxolane (CHEBI:26911) pre-flavunoidine(2+) (CHEBI:194090) is a oxolane (CHEBI:26911) tanegool (CHEBI:70196) is a oxolane (CHEBI:26911)

IUPAC Name

oxolane

Last Modified

08 July 2022

General Comment
2014-02-19	THF is occasionally found in human urine due to occupational exposure.