Compound
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate
An icosanoid anion arising from deprotonation of the carboxylic acid function of 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid; major species at pH 7.3.
Definition from ChEBI (CHEBI:132218), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound, anion
- Formula
- C20H29O5
- Mass
- 349.447 g/mol
- Charge
- -1
- InChIKey
- JIOJPWROWDJRKM-NNQKPOSRSA-M
- SMILES
- CC[C@@H](O)/C=C/C=CC/C=CC/C=CC=C[C@H](CCCC(=O)[O-])OO
- 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
3 statements
3 statements · 1 reference database · Subject: (5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate · Sources: Rhea
- (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:51968Inferred only
- (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)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinRhea RHEA:50268Inferred only
Reactions
3 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
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygen(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate
Catalysed by ALOX5
Reaction pageLeft to rightBalanced
Rhea RHEA:51968CC BY 4.0Reference data
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate+AH2CHEBI:133368+A+water
Reaction pageDirection not assertedBalanced
Rhea RHEA:52020CC BY 4.0Reference data
Other names
9 names
Resolves to: (5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate
- Also called
- (5S)-Hp-(18R)-H-(6E,8Z,11Z,14Z,16E)-EPE(5S)-Hp-(18R)-HEPE(5S)-HpHEPE(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoate18(R)-hydroxy-5(S)-HpEPE(1-)18(R)-hydroxy-5(S)-HpEPE(1−)5(S)-Hp-18(R)-HEPE(1-)5(S)-Hp-18(R)-HEPE(1−)
- Systematic name
- (5S,6E,8Z,11Z,14Z,16E,18R)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoate