Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-25 13:34:13 UTC |
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Update Date | 2022-03-07 02:50:59 UTC |
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HMDB ID | HMDB0010597 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) |
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Description | PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. 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. PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phosphatidylglycerol 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 phosphatidylglycerol increases during fetal development. Phosphatidylglycerol 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. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C44H75O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h11,13-14,16-18,20-21,24,26,30,32,41-42,45-46H,3-10,12,15,19,22-23,25,27-29,31,33-40H2,1-2H3,(H,49,50)/b13-11-,16-14-,18-17-,21-20-,26-24-,32-30-/t41-,42+/m0/s1 |
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Synonyms | Value | Source |
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1-(9Z-Hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-(9Z-Hexadecenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Palmitoleoyl-2-docosapentaenoyl-sn-glycero-3-phosphoglycerol | HMDB | 1-Palmitoleoyl-2-osbondoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(16:1/22:5) | HMDB | GPG(16:1N7/22:5N6) | HMDB | GPG(16:1W7/22:5W6) | HMDB | GPG(38:6) | HMDB | PG(16:1/22:5) | HMDB | PG(16:1N7/22:5N6) | HMDB | PG(16:1W7/22:5W6) | HMDB | PG(38:6) | HMDB | Phosphatidylglycerol(16:1/22:5) | HMDB | Phosphatidylglycerol(16:1n7/22:5n6) | HMDB | Phosphatidylglycerol(16:1W7/22:5W6) | HMDB | Phosphatidylglycerol(38:6) | HMDB | 1-(9Z-Hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoglycerol | HMDB | PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | Lipid Annotator |
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Chemical Formula | C44H75O10P |
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Average Molecular Weight | 795.0341 |
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Monoisotopic Molecular Weight | 794.509785132 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxyphosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C44H75O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h11,13-14,16-18,20-21,24,26,30,32,41-42,45-46H,3-10,12,15,19,22-23,25,27-29,31,33-40H2,1-2H3,(H,49,50)/b13-11-,16-14-,18-17-,21-20-,26-24-,32-30-/t41-,42+/m0/s1 |
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InChI Key | KQHAYNITKZCSTB-MZAXSNJMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphoglycerols |
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Direct Parent | Phosphatidylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0069266)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0069271)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0069274)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0069275)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0069288)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0069289)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0069293)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0069294)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0069297)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0078008)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078017)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078021)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0078032)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0078041)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078044)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0093282)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:1(9Z)) (PathBank: SMP0093285)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0093299)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0093311)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0093312)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0093317)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0093320)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0069267)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069276)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0069277)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0069281)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069286)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0069287)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z)) (PathBank: SMP0078009)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0078014)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0078022)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0078028)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0078033)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0078047)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078049)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0093283)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0093291)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0093306)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069263)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0078005)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:1(9Z)) (PathBank: SMP0078018)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0093278)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0093301)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069258)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0069282)
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5445.0 | Standard polar | 33892256 | PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4688.2 | Standard non polar | 33892256 | PG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5606.2 | Semi standard non polar | 33892256 |
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