PGP(18:0/18:1(9Z)) (BioCAD00000025765)

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Metabolite Card

Formula: C42H82O13P2 (856.523)
SMILES: [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC

Synonyms [en]

PGP(18:0/18:1n9); 1-stearoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate); PGP(18:0/18:1(9Z)); [(2~{R})-3-[hydroxy-[(2~{S})-2-hydroxy-3-phosphonooxy-propoxy]phosphoryl]oxy-2-[(~{Z})-octadec-9-enoyl]oxy-propyl] octadecanoate; PGP(18:0\/18:1(9Z)); 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

PGP(18:0/18:1(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: BioCAD00000025765). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

PGP(18:0/18:1(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(18:0/18:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of oleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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

  • CAS Registry Number:
  • PubChem CID: 53481824
  • ChEBI:
  • HMDB: HMDB0013506
  • LipidMaps:
  • KEGG:
  • BioCyc:
  • NCBI MeSH:
  • Wikipedia:
Other DBLinks
  • PubChem: 53481824
  • HMDB: HMDB0013506
  • Coconut NaturalProduct: CNP0572221.1

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0001101 phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z))
PathBank:SMP0028155 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))
PathBank:SMP0028159 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028163 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))
PathBank:SMP0028167 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))
PathBank:SMP0028171 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028175 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))
PathBank:SMP0028179 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))
PathBank:SMP0028183 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))
PathBank:SMP0028187 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))
PathBank:SMP0028191 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))
PathBank:SMP0028195 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)
PathBank:SMP0028199 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0028203 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0069605 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))
PathBank:SMP0069609 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))
PathBank:SMP0069613 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)
PathBank:SMP0069618 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))
PathBank:SMP0069622 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))
PathBank:SMP0069626 Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)
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