Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 08:46:12 UTC |
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Update Date | 2022-11-30 19:26:41 UTC |
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HMDB ID | HMDB0116618 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) |
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Description | PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylglycerol - 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(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of osbond acid at the C-1 position and one chain of osbond acid at the C-2 position. 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 (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 cardiolipin synthesis. |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C50H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-49(53)57-45-48(46-59-61(55,56)58-44-47(52)43-51)60-50(54)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,35-38,47-48,51-52H,3-10,15-16,21-22,27-28,33-34,39-46H2,1-2H3,(H,55,56)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t47-,48+/m0/s1 |
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Synonyms | Value | Source |
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1-osbondoyl-2-osbondoyl-sn-glycero-3-phospho-(1'-glycerol) | SMPDB, HMDB | 1-osbondoyl-2-osbondoyl-sn-glycero-3-phosphoglycerol | SMPDB, HMDB | PG(22:5/22:5) | SMPDB, HMDB | PG(22:5n6/22:5n6) | SMPDB, HMDB | PG(22:5w6/22:5w6) | SMPDB, HMDB | PG(44:10) | SMPDB, HMDB | Phosphatidylglycerol(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | SMPDB, HMDB | Phosphatidylglycerol(22:5/22:5) | SMPDB, HMDB | Phosphatidylglycerol(22:5n6/22:5n6) | SMPDB, HMDB | Phosphatidylglycerol(22:5w6/22:5w6) | SMPDB, HMDB | Phosphatidylglycerol(44:10) | SMPDB, HMDB | PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | SMPDB | PG(22:5/22:5) | Lipid Annotator | PG(44:10) | Lipid Annotator | GPG(44:10) | Lipid Annotator, HMDB | 1,2-diosbondoyl-rac-glycero-3-phosphoglycerol | Lipid Annotator, HMDB | Phosphatidylglycerol(22:5/22:5) | Lipid Annotator | 1,2-di(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-rac-glycero-3-phospho-(1'-glycerol) | Lipid Annotator, HMDB | 1,2-di(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-rac-glycero-3-phosphoglycerol | Lipid Annotator, HMDB | GPG(22:5/22:5) | Lipid Annotator, HMDB | [(2R)-2,3-Bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinate | Generator, HMDB |
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Chemical Formula | C50H79O10P |
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Average Molecular Weight | 871.146 |
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Monoisotopic Molecular Weight | 870.541085742 |
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IUPAC Name | [(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid |
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Traditional Name | (2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic 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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)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/C50H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-49(53)57-45-48(46-59-61(55,56)58-44-47(52)43-51)60-50(54)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,35-38,47-48,51-52H,3-10,15-16,21-22,27-28,33-34,39-46H2,1-2H3,(H,55,56)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t47-,48+/m0/s1 |
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InChI Key | CZOCCWRPXOTSIM-GWXFZNBXSA-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 | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029973)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029974)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029975)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029976)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0029977)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0029979)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029980)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029981)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029982)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029983)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029984)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029985)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029986)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029987)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0029988)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0029989)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029990)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029991)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029992)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029993)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029994)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029995)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029996)
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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 | |
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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(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 6355.6 | Standard polar | 33892256 | PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5152.7 | Standard non polar | 33892256 | PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 6212.6 | Semi standard non polar | 33892256 |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 10V, Positive-QTOF | splash10-0h4o-4116082190-fa4bda7ca15d4592bd0d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 20V, Positive-QTOF | splash10-0m2c-8159073640-6c53e366c32575ad068b | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 40V, Positive-QTOF | splash10-0adr-9028023220-cac19f8f47521af5dc65 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 10V, Negative-QTOF | splash10-02di-1109040140-db55e7673d5dc3023d98 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 20V, Negative-QTOF | splash10-004i-6319120100-020f4aabf544d956def5 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 40V, Negative-QTOF | splash10-004i-9001000000-c8c3ca1aa1419bccf9e6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 10V, Negative-QTOF | splash10-014i-0000000090-d9333c3c33801ebe8fe4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 20V, Negative-QTOF | splash10-016r-0109130090-741cca30e967ab992149 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 40V, Negative-QTOF | splash10-016r-0309130090-2bf2d71783d63ef1c00d | 2021-09-25 | Wishart Lab | View Spectrum |
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Pathways | |
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