Compound
(18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate
An 18-HEPE(1−) that is the conjugate base of 18(S)-HEPE, arising from deprotonation of the carboxylic acid group; major species at pH 7.3.
Definition from ChEBI (CHEBI:132083), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound, anion
- Formula
- C20H29O3
- Mass
- 317.449 g/mol
- Charge
- -1
- InChIKey
- LRWYBGFSVUBWMO-OKIFYYRFSA-M
- SMILES
- CC[C@H](O)/C=C/C=CC/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
2 entities
2 entities reached.
0 reported hops2 assembled from the scaffold
What the reference databases state
Chemical structure
- (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is the enantiomer of (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundChEBI CHEBI:132083Inferred only
Statements
4 statements
4 statements · 1 reference database · Subject: (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate · Sources: Rhea
- (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:50204Inferred only
- (5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate is converted to (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateCompoundRhea RHEA:50204Inferred only
- (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of ALOX5ProteinRhea RHEA:50204Inferred only
- (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate is a substrate of PTGS2ProteinRhea RHEA:50200Inferred only
Reactions
2 reactions
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate+AH2+dioxygen(18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:50200CC BY 4.0Reference data
(18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+dioxygen(5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate
Catalysed by ALOX5
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:50204CC BY 4.0Reference data
Other names
4 names
Resolves to: (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate
- Also called
- (18S)-H-(5Z,8Z,11Z,14Z,16E)-EPE(18S)-HEPE(18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-icosapentaenoate
- Systematic name
- (5Z,8Z,11Z,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoate