Compound

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

A complex mixture of phospholipids; glycolipids; and triglycerides; with substantial amounts of phosphatidylcholines; phosphatidylethanolamines; and phosphatidylinositols, which are sometimes loosely termed as 1,2-diacyl-3-phosphocholines. Lecithin is a component of the cell membrane and commercially extracted from soybeans and EGG yolk. The emulsifying and surfactant properties are useful in food additives and for forming organogels (gels).

Definition from MeSH (D054709), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:73003ChEBI

Open in the graph

Structure

2D depiction

No three-dimensional record for this entry.

Class: Organic compound
Formula: C44H80NO8P
Mass: 782.082 g/mol
Charge: 0
InChIKey: IIZPXYDJLKNOIY-JXPKJXOSSA-N
SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)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

17 entities

17 entities reached.

0 reported hops17 assembled from the scaffold

Show the remaining 5

What the reference databases state

Chemical structure

1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine has the functional parent arachidonic acidCompoundChEBI CHEBI:73003Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine has the functional parent hexadecanoic acidCompoundChEBI CHEBI:73003Inferred only

Statements

24 statements

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

Order

1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of LCATProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of LCATProteinRhea RHEA:53448Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G15ProteinRhea RHEA:38771Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G15ProteinRhea RHEA:38775Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G1BProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G3ProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4AProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4BProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4BProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4CProteinRhea RHEA:63780Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4CProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4CProteinRhea RHEA:40427Inferred only

Show the remaining 12

1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4DProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4EProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G4FProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G5ProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLA2G6ProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLAAT2ProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLAAT3ProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLAAT3ProteinRhea RHEA:40427Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLAAT4ProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PLAAT5ProteinRhea RHEA:45476Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PNPLA8ProteinRhea RHEA:40571Inferred only
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine is a substrate of PNPLA8ProteinRhea RHEA:40427Inferred only

Reactions

9 reactions

(5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA+1-hexadecanoyl-sn-glycero-3-phosphocholine1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+coenzyme A(4-)
Catalysed by LPCAT3 or MBOAT7
Reaction pageLeft to rightBalanced
Rhea RHEA:35999CC BY 4.0Reference data
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+N-(acetyl)-sphing-4-enine1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enine+1-hexadecanoyl-sn-glycero-3-phosphocholine
Catalysed by PLA2G15
Reaction pageLeft to rightBalanced
Rhea RHEA:38771CC BY 4.0Reference data
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+water1-hexadecanoyl-sn-glycero-3-phosphocholine+(5Z,8Z,11Z,14Z)-eicosatetraenoate+hydron
Catalysed by PLA2G6 or PLA2G1B or LCAT or PLA2G4B or PLA2G5 or PLA2G4A or PLAAT3 or PLA2G4E or PLA2G4F or PLA2G4D or PNPLA8 or PLA2G3 and 1 more alternative
Reaction pageLeft to rightBalanced
Rhea RHEA:40427CC 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
1-hexadecanoyl-2-(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+1-hexadecanoyl-sn-glycero-3-phosphocholine+hydron
Catalysed by PLAAT5
Reaction pageLeft to rightBalanced
Rhea RHEA:45476CC BY 4.0Reference data
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+cholesterolcholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate+1-hexadecanoyl-sn-glycero-3-phosphocholine
Catalysed by LCAT
Reaction pageLeft to rightBalanced
Rhea RHEA:53448CC BY 4.0Reference data
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine+a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine1-O-(1Z)-alkenyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine+1-hexadecanoyl-sn-glycero-3-phosphocholine
Catalysed by PLA2G4C
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:63780CC 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 rightBalanced
Rhea RHEA:63788CC BY 4.0Reference data

Other names

30 names

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

Also called: 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphocholine1-O-hexadecanoyl-2-O-arachidonoyl-sn-glycero-3-phosphocholine1-palmitoyl-2-arachidonoyl-GPC1-palmitoyl-2-arachidonoyl-GPC (16:0/20:4)1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine1-Palmitoyl-2-arachidonyl-gpc1-Palmitoyl-2-arachidonyl-phosphatidylcholineGPC(16:0/20:4)GPCho(16:0/20:4)GPCho(16:0/20:4omega6)GPCho(16:0/20:4ω6)GPCho(16:0/5Z,8Z,11Z,14Z-20:4)GPCho(36:4)LecithinPAPCPC 16:0/20:4(5Z,8Z,11Z,14Z)PC 36:4PC(16:0/20:4(5Z,8Z,11Z,14Z))PC(16:0/20:4)PC(16:0/20:4omega6)PC(16:0/20:4ω6)PC(36:4)PC[16:0/20:4(5Z,8Z,11Z,14Z)]Phosphatidylcholine(16:0/20:4)Phosphatidylcholine(16:0/20:4omega6)Phosphatidylcholine(16:0/20:4w6)Phosphatidylcholine(16:0/20:4ω6)Phosphatidylcholine(36:4)
Systematic name: (2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl 2-(trimethylammonio)ethyl phosphate(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate