Compound

(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

A polyunsaturated fatty acid anion that is the conjugate base of 13S,14S-epoxy-DHA, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:131958), read 2026-09-23. CC BY 4.0.

CHEBI:131958ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C22H29O3
Mass: 341.471 g/mol
Charge: -1
InChIKey: FFAHMRSFNLJTHE-WGHUZSCTSA-M
SMILES: CC/C=CC/C=CC[C@@H]1O[C@H]1/C=C/C=C/C=CC/C=CCCC(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

What the reference databases state

Statements

5 statements

5 statements · 1 reference database · Subject: (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate · Sources: Rhea

Order

(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate is converted to (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateCompoundRhea RHEA:53532Inferred only
(14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate is converted to (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateCompoundRhea RHEA:53532Inferred only
(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate is metabolised by GSTM4ProteinRhea RHEA:53508Inferred only
(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate is a substrate of ALOX12ProteinRhea RHEA:53532Inferred only
(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate is a substrate of LTC4SProteinRhea RHEA:53508Inferred only

Reactions

3 reactions

(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate+glutathione(13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate
Catalysed by GSTM4 or LTC4S
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53508CC BY 4.0Reference data
(14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate+water
Catalysed by ALOX12
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:53532CC BY 4.0Reference data
(13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate+waterCHEBI:137442
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:53536CC BY 4.0Reference data

Other names

5 names

Resolves to: (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

Also called: (13S,14S)-epoxy-DHA(1-)(13S,14S)-epoxy-DHA(1−)(13S,14S)-epoxy-maresin(1-)(13S,14S)-epoxy-maresin(1−)
Systematic name: (4Z,7Z,9E,11E)-12-{(2S,3S)-3-[(2Z,5Z)-octa-2,5-dien-1-yl]oxiran-2-yl}dodeca-4,7,9,11-tetraenoate