Compound

2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine

A lysophosphatidylcholine 20:4 in which the acyl group is specified as arachidonoyl and is located at position 2.

Definition from ChEBI (CHEBI:76079), read 2026-09-23. CC BY 4.0.

CHEBI:76079ChEBI

Open in the graph

Structure

2D depiction

Class: Organic compound
Formula: C28H50NO7P
Mass: 543.682 g/mol
Charge: 0
InChIKey: IGJKYDBBINVMLH-JXRLJXCWSA-N
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O[C@H](CO)COP(=O)([O-])OCC[N+](C)(C)C
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

Chemical structure

2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine has the functional parent arachidonic acidCompoundChEBI CHEBI:76079Inferred only

Statements

9 statements

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

Order

2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is converted to 2-(prostaglandin G2)-sn-glycero-3-phosphocholineCompoundRhea RHEA:54212Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of ASPGProteinRhea RHEA:40827Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of ASPGProteinRhea RHEA:40959Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of LPGAT1ProteinRhea RHEA:74807Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of PLA2G6ProteinRhea RHEA:40827Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of PTGS2ProteinRhea RHEA:53680Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of PTGS2ProteinRhea RHEA:53676Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of PTGS2ProteinRhea RHEA:53684Inferred only
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine is a substrate of PTGS2ProteinRhea RHEA:54212Inferred only

Reactions

14 reactions

1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+N-(acetyl)-sphing-4-enine1-hexadecanoyl-N-(acetyl)-sphing-4-enine+2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
Catalysed by PLA2G15
Reaction pageLeft to rightBalanced
Rhea RHEA:38775CC BY 4.0Reference data
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+water2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+hexadecanoate+hydron
Catalysed by PLA2G4B or PLAAT3 or PNPLA8 or PLAAT2 or PLAAT4 or PLA2G4C
Reaction pageLeft to rightBalanced
Rhea RHEA:40571CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+watersn-glycerol 3-phosphocholine+(5Z,8Z,11Z,14Z)-eicosatetraenoate+hydron
Catalysed by PLA2G6 or ASPG
Reaction pageLeft to rightBalanced
Rhea RHEA:40827CC BY 4.0Reference data
22-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine1,2-di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+sn-glycerol 3-phosphocholine
Catalysed by ASPG
Reaction pageLeft to rightBalanced
Rhea RHEA:40959CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+water2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate+choline+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:41392CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+AH2+dioxygen2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalanced
Rhea RHEA:53676CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+AH2+dioxygen2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalanced
Rhea RHEA:53680CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+AH2+dioxygen2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine+A+water
Catalysed by PTGS2
Reaction pageLeft to rightBalanced
Rhea RHEA:53684CC BY 4.0Reference data
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+2dioxygen2-(prostaglandin G2)-sn-glycero-3-phosphocholine
Catalysed by PTGS2
Reaction pageLeft to rightBalanced
Rhea RHEA:54212CC BY 4.0Reference data
1-tetradecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+water2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+tetradecanoate+hydron
Catalysed by ABHD3
Reaction pageLeft to rightBalanced
Rhea RHEA:54396CC BY 4.0Reference data
1,2-di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine+2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine+hydron
Catalysed by PLA2G4E
Reaction pageLeft to rightBalanced
Rhea RHEA:55256CC BY 4.0Reference data
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+N-(acetyl)-sphing-4-enine1-octadecanoyl-N-(acetyl)-sphing-4-enine+2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
Catalysed by PLA2G15
Reaction pageLeft to rightBalanced
Rhea RHEA:57120CC BY 4.0Reference data

Show the remaining 2

Other names

13 names

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

Also called: 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholine2-arachidonoyl-GPC2-arachidonoyl-lysophosphatidylcholine2-arachidonoyllysophosphatidylcholineGPC(0:0/20:4)GPC(20:4)LPC 20:4LPC(0:0/20:4(5Z,8Z,11Z,14Z))LPC(20:4)PC 0:0/20:4(5Z,8Z,11Z,14Z)PC(0:0/20:4(5Z,8Z,11Z,14Z))
Systematic name: (2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate