Compound

1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine

A phosphatidylethanolamine 38:4 zwitterion obtained by transfer of a proton from the phosphate to the primary amino group of 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.

Definition from ChEBI (CHEBI:78268), read 2026-09-23. CC BY 4.0.

CHEBI:78268ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound
Formula: C43H78NO8P
Mass: 768.07 g/mol
Charge: 0
InChIKey: ANRKEHNWXKCXDB-BHFWLYLHSA-N
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)([O-])OCC[NH3+]
Look it up: ChEBI By InChIKey

Identity from ChEBI. 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

Chemical structure

1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine has the functional parent 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineCompoundChEBI CHEBI:146282Inferred only

Statements

6 statements

6 statements · 1 reference database · Subject: 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine · Sources: Rhea

Order

1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine is converted to 1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineCompoundRhea RHEA:63268Inferred only
1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine is converted to 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineCompoundRhea RHEA:63268Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine is a substrate of ALOX15BProteinRhea RHEA:63268Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLA2G4CProteinRhea RHEA:63788Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine is a substrate of PLA2G4CProteinRhea RHEA:63776Inferred only
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine is a substrate of PTDSS2ProteinRhea RHEA:41500Inferred only

Reactions

5 reactions

1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+L-seryl residue1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoserine+ethanolamine
Catalysed by PTDSS2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:41500CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+dioxygen1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Catalysed by ALOX15B
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:63268CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+1-O-hexadecyl-sn-glycero-3-phosphocholine1-octadecanoyl-sn-glycero-3-phosphoethanolamine+1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
Catalysed by PLA2G4C
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:63776CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+1-hexadecanoyl-sn-glycero-3-phosphocholine1-octadecanoyl-sn-glycero-3-phosphoethanolamine+1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
Catalysed by PLA2G4C
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:63788CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol+CDP-ethanolamine1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+CMP+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:80247CC BY 4.0Reference data

Other names

8 names

Resolves to: 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine

Also called: 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine1-stearoyl-2-arachidonoyl-GPE1-stearoyl-2-arachidonoyl-GPE (18:0/20:4)GPE(18:0/20:4(5Z,8Z,11Z,14Z))GPE(18:0/20:4)PE(18:0/20:4(5Z,8Z,11Z,14Z))PE(18:0/20:4)
Systematic name: 2-azaniumylethyl (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propyl phosphate