Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2008-09-25 13:34:16 UTC |
---|
Update Date | 2022-11-30 19:03:54 UTC |
---|
HMDB ID | HMDB0010600 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | PG(18:0/16:0) |
---|
Description | PG(18:0/16:0) 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(18:0/16:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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. |
---|
Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 |
---|
Synonyms | Value | Source |
---|
1-18:0-2-16:0-Phosphatidylglycerol | ChEBI | 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) | ChEBI | 1-Stearoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol | ChEBI | 18:0-16:0-PG | ChEBI | 2-Palmitoyl-1-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol) | ChEBI | GPG(18:0/16:0) | ChEBI | GPG(34:0) | ChEBI | PG(34:0) | ChEBI | Phosphatidylglycerol(18:0/16:0) | ChEBI | Phosphatidylglycerol(34:0) | ChEBI | 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphoglycerol | HMDB | PG(18:0/16:0) | Lipid Annotator |
|
---|
Chemical Formula | C40H79O10P |
---|
Average Molecular Weight | 751.023 |
---|
Monoisotopic Molecular Weight | 750.54108526 |
---|
IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid |
---|
Traditional Name | (2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC |
---|
InChI Identifier | InChI=1S/C40H79O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41-42H,3-36H2,1-2H3,(H,45,46)/t37-,38+/m0/s1 |
---|
InChI Key | WYVBOKLMHDFYQD-QPPIDDCLSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphoglycerols |
---|
Direct Parent | Phosphatidylglycerols |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | |
---|
Disposition | |
---|
Process | Naturally occurring processBiological processChemical reactionBiochemical pathway- Cardiolipin Biosynthesis (HMDB: HMDB0010600)
Metabolic pathway- Phospholipid Biosynthesis CL(18:0/16:0/18:0/16:0) (PathBank: SMP0001782)
- Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0) (PathBank: SMP0027929)
- Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z)) (PathBank: SMP0027930)
- Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0) (PathBank: SMP0027931)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0) (PathBank: SMP0027932)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z)) (PathBank: SMP0027933)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0) (PathBank: SMP0027934)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z)) (PathBank: SMP0027935)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z)) (PathBank: SMP0027936)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z)) (PathBank: SMP0027937)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0027938)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027939)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027940)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027941)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0) (PathBank: SMP0027942)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0) (PathBank: SMP0027943)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z)) (PathBank: SMP0027944)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0027945)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0) (PathBank: SMP0027946)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0) (PathBank: SMP0027947)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0027948)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0027949)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0) (PathBank: SMP0027950)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0) (PathBank: SMP0027951)
- Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0027952)
- Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0) (PathBank: SMP0027953)
- Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0) (PathBank: SMP0027954)
- Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0027955)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0027956)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0027957)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027958)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027959)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027960)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0027961)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027962)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027963)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027964)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0027965)
- Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027966)
Biochemical processCellular process |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:0/16:0) GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 10V, Positive-QTOF | splash10-0gej-3190520500-a00b3ffa9e03d33ff693 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 20V, Positive-QTOF | splash10-00p0-4191311100-1e8a98896f4f8de789fc | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 40V, Positive-QTOF | splash10-0570-9073220000-a49b913fab75609bd185 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 10V, Negative-QTOF | splash10-00lr-0190200200-babce605157fe57a566c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 20V, Negative-QTOF | splash10-00o0-4290100000-d54955c7c25f2a0024fd | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 40V, Negative-QTOF | splash10-004i-9030000000-f8fc91c44bd9eb3b3190 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 10V, Negative-QTOF | splash10-0002-0000000900-01f8acb19a844bd6d2dd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 20V, Negative-QTOF | splash10-053s-0090300400-7926d39d0fa0623a46d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:0/16:0) 40V, Negative-QTOF | splash10-053s-0190300400-98baa113a06477af5f07 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum |
|
---|