Compound
(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate
A 14,15-EET(1−) that is the conjugate base of (14S,15R)-EET, obtained by deprotonation of the carboxy group; major species at pH 7.3.
Definition from ChEBI (CHEBI:131964), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound, anion
- Formula
- C20H31O3
- Mass
- 319.465 g/mol
- Charge
- -1
- InChIKey
- JBSCUHKPLGKXKH-KZTFMOQPSA-M
- SMILES
- CCCCC[C@H]1O[C@H]1C/C=CC/C=CC/C=CCCCC(=O)[O-]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
3 entities
3 entities reached.
What the reference databases state
Chemical structure
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is the enantiomer of (14R,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundChEBI CHEBI:131964Inferred only
Statements
5 statements
5 statements · 1 reference database · Subject: (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate · Sources: Rhea
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is metabolised by EPHX2ProteinRhea RHEA:53992Inferred only
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is metabolised by EPHX2ProteinRhea RHEA:53996Inferred only
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ALOX12ProteinRhea RHEA:50284Inferred only
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ALOX15ProteinRhea RHEA:50284Inferred only
- (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ALOX15ProteinRhea RHEA:50288Inferred only
Reactions
5 reactions
(5Z,8Z,11Z,14Z)-eicosatetraenoate+reduced [NADPH--hemoprotein reductase]+dioxygen(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP1A1 or CYP1A2 or CYP3A4 or CYP2C8 or CYP2D6 or CYP2C9 or CYP2J2 or CYP4Z1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:49856CC BY 4.0Reference data
(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate+dioxygenCHEBI:132065
Reaction pageLeft to rightBalanced
Rhea RHEA:50284CC BY 4.0Reference data
(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate+dioxygenCHEBI:132068
Catalysed by ALOX15
Reaction pageLeft to rightBalanced
Rhea RHEA:50288CC BY 4.0Reference data
(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate+waterCHEBI:138003
Catalysed by EPHX2
Reaction pageLeft to rightBalanced
Rhea RHEA:53992CC BY 4.0Reference data
(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate+waterCHEBI:138006
Catalysed by EPHX2
Reaction pageLeft to rightBalanced
Rhea RHEA:53996CC BY 4.0Reference data
Other names
6 names
Resolves to: (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate
- Also called
- (14S,15R)-Ep-(5Z,8Z,11Z)-EtrE(14S,15R)-EpETrE(14S,15R)-EpETrE(1-)(14S,15R)-EpETrE(1−)(14S,15R)-epoxy-(5Z,8Z,11Z)-icosatrienoate
- Systematic name
- (5Z,8Z,11Z)-13-[(2S,3R)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoate