Compound

14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate

An icosanoid anion that is the conjugate base of 14,15-EET, obtained by deprotonation of the carboxy group; major species at pH 7.3.

Definition from ChEBI (CHEBI:84024), read 2026-09-23. CC BY 4.0.

CHEBI:84024ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound, anion
Formula: C20H31O3
Mass: 319.465 g/mol
Charge: -1
InChIKey: JBSCUHKPLGKXKH-ILYOTBPNSA-M
SMILES: CCCCCC1OC1C/C=CC/C=CC/C=CCCCC(=O)[O-]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

25 entities

25 entities reached.

0 reported hops25 assembled from the scaffold

Show the remaining 13

What the reference databases state

Statements

30 statements

30 statements · 2 reference databases · Subject: 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate · Sources: Human-GEM, Rhea

Order

(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundHuman-GEM MAR00954Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundHuman-GEM MAR00955Inferred only
(5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateCompoundHuman-GEM MAR00956Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is metabolised by CYP2C9ProteinRhea RHEA:51472Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is metabolised by EPHX1ProteinHuman-GEM MAR00957Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is metabolised by EPHX2ProteinHuman-GEM MAR00957Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of AASDHProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACAA1ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACAA2ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOT1ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOT2ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOT4ProteinHuman-GEM MAR01068Inferred only

Show the remaining 18

14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOT7ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOT8ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOX1ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACOX3ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACSF2ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ACSF3ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of AMACRProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of BAATProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of ECHS1ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of HADHProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of HADHAProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of HADHBProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of HSD17B10ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of HSD17B4ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of SLC27A1ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of SLC27A2ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of SLC27A3ProteinHuman-GEM MAR01068Inferred only
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate is a substrate of SLC27A4ProteinHuman-GEM MAR01068Inferred only

Reactions

13 reactions

11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoate+15-oxoprostaglandin E1+MAM00014x+(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate+MAM00254c+MAM00254m+MAM00254x+20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00274c+MAM00274r+MAM00276c+MAM00277c+MAM00278c+MAM00280c+MAM00282c+11beta-hydroxyandrost-4-ene-3,17-dione+11beta-hydroxyandrost-4-ene-3,17-dione+11beta-hydroxyandrost-4-ene-3,17-dione+MAM00293c+MAM00297c+MAM00298c+MAM00304c+MAM00306c+MAM00308c+MAM00318c+MAM00318r+MAM00319c+MAM00320c+MAM00321c+MAM00322c+MAM00323c+MAM00323r+MAM00324r+MAM00327c+MAM00327r+MAM00328c+MAM00328r+MAM00333r+12-oxo-(5Z,8Z,10E,14Z)-eicosatetraenoate+(13S)-hydroxy-(9Z,11E)-octadecadienoate+MAM00338c+MAM00340c+MAM00352r+13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00364c+14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+(15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate+MAM00378c+MAM00382c+15-deoxy-Delta(12,14)-prostaglandin J2+MAM00384c+MAM00386c+MAM00386r+MAM00386x+MAM00387c+MAM00387r+MAM00387x+MAM00388c+MAM00388r+MAM00388x+MAM00389c+MAM00389r+MAM00389x+15-oxoprostaglandin F2alpha+MAM00395c+16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00398x+17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00424m+MAM00425x+MAM00426c+18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM00430c+MAM00590c+MAM00595c+MAM00595r+MAM00598c+MAM00598r+MAM00602c+MAM00687m+MAM00687x+MAM01038n+MAM01039x+MAM01041n+MAM01046c+MAM01047c+MAM01049c+MAM01050c+MAM01051c+5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate+MAM01055c+MAM01120c+MAM01120r+MAM01122c+MAM01122r+MAM01150c+MAM01150m+MAM01150x+MAM01153c+MAM01153m+MAM01153r+MAM01153x+MAM01167c+MAM01168r+MAM01171c+MAM01171m+MAM01171x+MAM01172c+MAM01172m+MAM01172x+7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate+MAM01202c+MAM01208c+8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate+MAM01210c+MAM01213c+MAM01239c+(11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoate+(11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoate+MAM02368c+MAM02395n+MAM02395r+MAM02395x+MAM02396r+MAM02396x+malonaldehyde+MAM02538c+MAM02538n+MAM02649m+MAM02649x+prostaglandin E2+prostaglandin E3+prostaglandin H1+prostaglandin J2+MAM02797c+MAM02798c+MAM02799c+MAM02851c+MAM02852c+MAM02862c+MAM02863c+MAM02864c+MAM03055c+MAM03055r+MAM03055x+MAM03056cMAM10003e
Reaction pageLeft to rightBalance undeterminableGO:0005829, GO:0005777, GO:0005759, GO:0005783, GO:0005634, GO:0005615
Human-GEM MAR00036CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+proton+NADPH(4-)+dioxygen14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+water+NADP(3-)
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 15 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005829
Human-GEM MAR00954CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+FAD+water
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 15 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005829
Human-GEM MAR00955CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+FADH2+dioxygen14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+FAD+water
Catalysed by CYP3A43 or CYP2D6 or CYP3A5 or CYP2C18 or CYP2E1 or CYP2J2 or CYP1B1 or CYP2C9 or CYP2C8 or CYP1A1 or CYP1A2 or CYP4B1 and 15 more alternatives
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005783
Human-GEM MAR00956CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+waterMAM00364c
Catalysed by EPHX2 or EPHX1
Reaction pageLeft to rightBalancedEC 3.3.2.9, 3.3.2.10GO:0005829
Human-GEM MAR00957CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+ATP+CHEBI:1146900+2water+NAD(+)+dioxygenMAM00310c+CHEBI:15351+AMP+hydrogen peroxide+NADH(2-)+diphosphate(3-)
Catalysed by ACAA1 or HSD17B10 or HADHA or ACOX3 or ACOT7 or ACOT8 or ACOT2 or ECHS1 or SLC27A1 or HSD17B4 or BAAT or HADHB and 12 more alternatives
Reaction pageLeft to rightUnbalancedEC 1.1.1.35, 1.3.3.6, 2.3.1.176, 2.3.1.16, 3.1.2.2, 4.2.1.17, 5.1.99.4, 6.2.1.-GO:0005829
Human-GEM MAR01068CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+ATP+water14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+ADP+proton+phosphate(3-)
Reaction pageLeft to rightBalancedGO:0005829, GO:0005615
Human-GEM MAR10147CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR10216CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate
Reaction pageLeft to rightBalancedGO:0005615, GO:0005829
Human-GEM MAR11575CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+waterCHEBI:84029
Catalysed by EPHX2 or EPHX3
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:44040CC BY 4.0Reference data
(5Z,8Z,11Z,14Z)-eicosatetraenoate+reduced [NADPH--hemoprotein reductase]+dioxygen14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Catalysed by CYP2C9
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:51472CC BY 4.0Reference data
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate+ATP(4-)+coenzyme A(4-)14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoyl-CoA+AMP+diphosphate(3-)
Catalysed by ACSL4 or ACSL3 or ACSL1 or ACSL5
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:52016CC BY 4.0Reference data

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Other names

6 names

Resolves to: 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate

Also called: 14,15-Ep-(5Z,8Z,11Z)-ETrE14,15-EpETE14,15-EpETrE(1-)14,15-EpETrE(1−)14,15-epoxy-(5Z,8Z,11Z)-icosatrienoate
Systematic name: (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate