PA(16:0/16:0) (BioCAD00000019778)

blood

Metabolite Card

Formula: C35H69O8P (648.473)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC

Synonyms [en]

PA(16:0/16:0); PA(32:0); dipalmitoyl phosphatidic acid; 1,2-Dipalmitoyl-3-sn-phosphatidic acid; 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid; Phosphatidic acid(32:0)

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

PA(16:0/16:0). 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: BioCAD00000019778). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

PA(16:0/16:0) 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(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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
  • CAS Registry Number: 7091-44-3
  • PubChem: 446066
  • ChEBI: ChEBI:73246
  • HMDB: HMDB0000674
  • HMDB: HMDB00674
  • LipidMaps: LMGP10010027
  • KEGG: C00416
  • BioCyc: CPD0-1422
  • NCBI MeSH: dipalmitoylphosphatidic acid
  • RefMet: RM0138812
  • MoNA: FiehnHILIC000873
  • MoNA: FiehnHILIC002430
  • MoNA: HMDB0000674_ms_ms_933
  • MoNA: HMDB0000674_ms_ms_934
  • MoNA: HMDB0000674_ms_ms_935
  • Metlin: METLIN_81205
  • Coconut NaturalProduct: CNP0238474.2

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN0-6705 2.3.1.51 1-PALMITOYLGLYCEROL-3-PHOSPHATE + Palmitoyl-ACPs --> CPD0-1422 + ACP
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0120706 Glycerol Kinase Deficiency
PathBank:SMP0120814 Familial Lipoprotein Lipase Deficiency
PathBank:SMP0026954 Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)
PathBank:SMP0026958 Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))
PathBank:SMP0026962 Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0026966 Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)
PathBank:SMP0026970 Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0026974 Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)
PathBank:SMP0026978 Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))
PathBank:SMP0026982 Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0026986 Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)
PathBank:SMP0026990 Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0026994 Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)
PathBank:SMP0026998 Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))
PathBank:SMP0027002 Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0027006 Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)
PathBank:SMP0027010 Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0027014 Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)
PathBank:SMP0027018 Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))
PathBank:SMP0027022 Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))
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