Compound

2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine

A 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion obtained by transfer of a proton from the phosphate to the amino group of 2-oleoyl-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.

Definition from ChEBI (CHEBI:76088), read 2026-09-23. CC BY 4.0.

CHEBI:76088ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound
Formula: C23H46NO7P
Mass: 479.595 g/mol
Charge: 0
InChIKey: NOVZJYYJYIFXJC-MZMPXXGTSA-N
SMILES: CCCCCCCC/C=CCCCCCCCC(=O)O[C@H](CO)COP(=O)([O-])OCC[NH3+]
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

4 entities

4 entities reached.

0 reported hops4 assembled from the scaffold

What the reference databases state

Statements

5 statements

5 statements · 1 reference database · Subject: 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine · Sources: Rhea

Order

2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine is a substrate of DDHD2ProteinRhea RHEA:45132Inferred only
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine is a substrate of LPGAT1ProteinRhea RHEA:70579Inferred only
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine is a substrate of LPGAT1ProteinRhea RHEA:70591Inferred only
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine is a substrate of PLA2G15ProteinRhea RHEA:38827Inferred only
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine is a substrate of PLA2G4EProteinRhea RHEA:55260Inferred only

Reactions

6 reactions

1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+N-(acetyl)-sphing-4-enine2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+1-hexadecanoyl-N-(acetyl)-sphing-4-enine
Catalysed by PLA2G15
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:38827CC BY 4.0Reference data
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+water2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+hexadecanoate+hydron
Catalysed by DDHD2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:45132CC BY 4.0Reference data
21,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineN,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+hydron
Catalysed by PLA2G4E
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:55260CC BY 4.0Reference data
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+octadecanoyl-CoA1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+coenzyme A(4-)
Catalysed by LPGAT1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:70579CC BY 4.0Reference data
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+hexadecanoyl-CoA1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+coenzyme A(4-)
Catalysed by LPGAT1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:70591CC BY 4.0Reference data
2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+(9Z)-octadecenoyl-CoA1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+coenzyme A(4-)
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:86883CC BY 4.0Reference data

Other names

8 names

Resolves to: 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine

Also called: 2-oleoyllysophosphatidylethanolamine zwitterionLPE 18:1LPE(18:1)LPE[0:0/18:1(omega-9)] zwitterionLPE[0:0/18:1(ω-9)] zwitterionPE 0:0/18:1(9Z)PE(0:0/18:1(9Z))
Systematic name: 2-azaniumylethyl (2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propyl phosphate