PGP(18:1(11Z)/16:1(9Z)) (BioCAD00000025777)

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Metabolite Card

Formula: C40H76O13P2 (826.4761)
SMILES: CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)COP(=O)(O)O)OC(=O)CCCCCCC\C=C/CCCCCC

Synonyms [en]

PGP(18:1(11Z)/16:1(9Z)); 1-vaccenoyl-2-palmitoleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate); PGP(18:1W7/16:1W7); PGP(18:1w7\/16:1w7); PGP(18:1(11Z)\/16:1(9Z)); [(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

PGP(18:1(11Z)/16:1(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: BioCAD00000025777). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

PGP(18:1(11Z)/16:1(9Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols 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. PGP(18:1(11Z)/16:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.

Entity Information

DBLinks

Other DBLinks
  • PubChem: 53481836
  • ChEBI: ChEBI:180737
  • HMDB: HMDB0013518
  • Coconut NaturalProduct: CNP0113525.1

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0028459 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))
PathBank:SMP0028463 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028467 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))
PathBank:SMP0028471 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))
PathBank:SMP0028475 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028479 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
PathBank:SMP0028483 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0028487 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028491 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))
PathBank:SMP0028495 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))
PathBank:SMP0069917 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))
PathBank:SMP0069921 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0069926 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))
PathBank:SMP0069930 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))
PathBank:SMP0069934 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0069938 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
PathBank:SMP0069942 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0069946 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0069950 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))
PathBank:SMP0069954 Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))
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