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 13:34:38 UTC |
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Update Date | 2022-03-07 02:51:00 UTC |
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HMDB ID | HMDB0010622 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PG(18:1(11Z)/18:3(9Z,12Z,15Z)) |
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Description | PG(18:1(11Z)/18:3(9Z,12Z,15Z)) 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(18:1(11Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. 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)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C42H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12-15,18,20,39-40,43-44H,3-5,7,9-11,16-17,19,21-38H2,1-2H3,(H,47,48)/b8-6-,14-12-,15-13-,20-18-/t39-,40+/m0/s1 |
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Synonyms | Value | Source |
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1-(11Z-Octadecenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Vaccenoyl-2-a-linolenoyl-sn-glycero-3-phosphoglycerol | HMDB | 1-Vaccenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:1/18:3) | HMDB | GPG(18:1N7/18:3N3) | HMDB | GPG(18:1W7/18:3W3) | HMDB | GPG(36:4) | HMDB | PG(18:1/18:3) | HMDB | PG(18:1N7/18:3N3) | HMDB | PG(18:1W7/18:3W3) | HMDB | PG(36:4) | HMDB | Phosphatidylglycerol(18:1/18:3) | HMDB | Phosphatidylglycerol(18:1n7/18:3n3) | HMDB | Phosphatidylglycerol(18:1W7/18:3W3) | HMDB | Phosphatidylglycerol(36:4) | HMDB | 1-(11Z-Octadecenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphoglycerol | HMDB | PG(18:1(11Z)/18:3(9Z,12Z,15Z)) | Lipid Annotator |
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Chemical Formula | C42H75O10P |
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Average Molecular Weight | 771.0127 |
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Monoisotopic Molecular Weight | 770.509785132 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]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)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C42H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12-15,18,20,39-40,43-44H,3-5,7,9-11,16-17,19,21-38H2,1-2H3,(H,47,48)/b8-6-,14-12-,15-13-,20-18-/t39-,40+/m0/s1 |
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InChI Key | QUMYVZXTAFJZPC-KEXKQFALSA-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(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0099638)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0099644)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0099647)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0099648)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0099657)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0099636)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099640)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099641)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0099658)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085168)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0099637)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0099639)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0099656)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0085169)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0099633)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099634)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099635)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0099642)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0099643)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099649)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099650)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099653)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081849)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0081854)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081858)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081861)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0081862)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081863)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085170)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085171)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085174)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085176)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085177)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085180)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085181)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085182)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085183)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085184)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085185)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085186)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085187)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085188)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085189)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085192)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085194)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085195)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099645)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099646)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099651)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099652)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099654)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099655)
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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 IndicesUnderivatized | Show more...
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