PA(18:1(11Z)/18:1(9Z)) (BioCAD00000021733)

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Metabolite Card

Formula: C39H73O8P (700.5043)
SMILES: [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC

Synonyms [en]

PA(18:1(11Z)/18:1(9Z)); 1-Vaccenoyl-2-oleoyl-sn-glycero-3-phosphate; [(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid; 1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-phosphatidic acid; Q27161723; Phosphatidic acid(18:1n7\/18:1n9)

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

PA(18:1(11Z)/18:1(9Z)). 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000021733). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

PA(18:1(11Z)/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:1(11Z)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776).

Entity Information

DBLinks

Other DBLinks
  • PubChem: 53478603
  • ChEBI: ChEBI:89527
  • HMDB: HMDB0007863
  • HMDB: HMDB07863
  • KEGG: C00416
  • BioCyc: L-PHOSPHATIDATE
  • Wikipedia: Lecithin
  • Metlin: METLIN_59314
  • Coconut NaturalProduct: CNP0362356.1

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0028607 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))
PathBank:SMP0028611 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028615 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))
PathBank:SMP0028619 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028623 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))
PathBank:SMP0028627 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
PathBank:SMP0028631 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028635 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))
PathBank:SMP0028639 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028643 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))
PathBank:SMP0028647 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))
PathBank:SMP0028651 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028655 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))
PathBank:SMP0028659 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028663 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))
PathBank:SMP0028667 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))
PathBank:SMP0028671 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0033054 De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(8Z,11Z,14Z))
PathBank:SMP0070504 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0070508 Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)
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