Compound
(5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate
An epoxy hydroxyeicosapentaenoate anion arising from deprotonation of the carboxylic acid function of 5(S),6(S)-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoic acid; major species at pH 7.3.
Definition from ChEBI (CHEBI:132219), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound, anion
- Formula
- C20H27O4
- Mass
- 331.432 g/mol
- Charge
- -1
- InChIKey
- ZPAJZAMPZXISSE-SIPVSCHGSA-M
- SMILES
- CC[C@@H](O)/C=C/C=CC/C=CC=CC=C[C@@H]1O[C@H]1CCCC(=O)[O-]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
1 entity
1 entities reached.
0 reported hops1 assembled from the scaffold
What the reference databases state
Statements
2 statements
2 statements · 1 reference database · Subject: (5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate · Sources: Rhea
- (5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:50268Inferred only
- (5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate is a substrate of LTA4HProteinRhea RHEA:50272Inferred only
Reactions
2 reactions
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate(5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate+water
Catalysed by ALOX5
Reaction pageLeft to rightBalanced
Rhea RHEA:50268CC BY 4.0Reference data
(5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate+waterCHEBI:91000
Catalysed by LTA4H
Reaction pageLeft to rightBalanced
Rhea RHEA:50272CC BY 4.0Reference data
Other names
8 names
Resolves to: (5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate
- Also called
- (5S,6S)-Ep-(18R)-H-(7E,9E,11Z,14Z,16E)-EPE(5S,6S)-Ep-(18R)-HEPE(5S,6S)-epoxy-(18R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoate18(R)-hydroxy-5(S),6(S)-EpEPE(1-)18(R)-hydroxy-5(S),6(S)-EpEPE(1−)5(S),6(S)-epoxy-18(R)-HEPE(1-)5(S),6(S)-epoxy-18(R)-HEPE(1−)
- Systematic name
- 4-{(2S,3S)-3-[(1E,3E,5Z,8Z,10E,12R)-12-hydroxytetradeca-1,3,5,8,10-pentaen-1-yl]oxiran-2-yl}butanoate