Record Information |
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Version | 1.0 |
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Creation Date | 2016-10-03 18:13:38 UTC |
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Update Date | 2020-04-22 15:42:56 UTC |
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BMDB ID | BMDB0011149 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | LysoPC(O-18:0) |
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Description | LysoPC(O-18:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(O-18:0/0:0), in particular, consists of one octadecyl chain to the C-1 atom, and one octadecyl to the C-2 atom. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. |
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Structure | |
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Synonyms | Value | Source |
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1-O-Octadecylglycerol-3-phosphatidylcholine | HMDB | 1-Octadecyl-sn-glycero-3-phosphocholine | HMDB | 1-Stearyl-GPC | HMDB | 1-Stearyl-GPC (O-18:0) | HMDB | GPC(O-18:0) | HMDB | GPC(O-18:0/0:0) | HMDB | LPC (O-18:0) | HMDB | LysoPC(18:0E/0:0) | HMDB | LysoPC(O-18:0) | HMDB | PC(O-18:0/0:0) | HMDB | LysoPC(DM18:0) | HMDB | 1-O-Octadecyl-sn-glycero-3-phosphocholine | HMDB | 1-O-Octadecyl-sn-glyceryl-3-phosphorylcholine | HMDB | 1-Octadecyl-GPC | HMDB | 1-Octadecyl-lysophosphatidylcholine | HMDB | 1-Octadecylglycero-3-phosphocholine | HMDB | GPC(18:0) | HMDB | GPC(18:0/0:0) | HMDB | LPC(18:0) | HMDB | LPC(18:0/0:0) | HMDB | LPC(O-18:0) | HMDB | LPC(O-18:0/0:0) | HMDB | Lyso-platelet-activating factor | HMDB | LysoPC(18:0) | HMDB | LysoPC(18:0/0:0) | HMDB | Lysophosphatidylcholine(18:0) | HMDB | Lysophosphatidylcholine(18:0/0:0) | HMDB | Lysophosphatidylcholine(O-18:0) | HMDB | Lysophosphatidylcholine(O-18:0/0:0) | HMDB | LysoPC(O-18:0/0:0) | HMDB |
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Chemical Formula | C26H56NO6P |
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Average Molecular Weight | 509.6997 |
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Monoisotopic Molecular Weight | 509.384525041 |
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IUPAC Name | (2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C |
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InChI Identifier | InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1 |
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InChI Key | XKBJVQHMEXMFDZ-AREMUKBSSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond. |
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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 | Glycerophosphocholines |
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Direct Parent | Monoalkylglycerophosphocholines |
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Alternative Parents | |
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Substituents | - Monoalkylglycerophosphocholine
- Phosphocholine
- Glycerol ether
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Secondary alcohol
- Ether
- Dialkyl ether
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Organic salt
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Expected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cell membrane
- Intracellular membrane
- Membrane
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-5930000000-c002f9346ff27ec388a3 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0002-9460000000-f8bf856a15fd2cd2fa22 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01p9-9123230000-9e5018d60ea3b2b28b32 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ugr-9455200000-0c72dc03f55ca1a4599e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f79-9231000000-adbce76401a5b20f74d5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0010490000-78228db3f0e06f9d298c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ar0-2160920000-56a3704799b8868294e2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00or-9280000000-a127711d12f38e903413 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000090000-92389686f000bb55e113 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0000090000-92389686f000bb55e113 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0000930000-3fa7cb0f3d40c52c6b6a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000090000-0092c5cfc59f1e835b62 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0020290000-1cacf188cd006762529a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9210100000-3e2f6987fc891e79e2c0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000090000-ac3949a1bc7527be80e6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0110690000-b1a4faf5ff77d30fbafc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-0110910000-2f268286db3bc04e9cec | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0il0-1900160000-4dc04f9d727b989bed34 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ik9-1710190000-87893f3898856e238ceb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ik9-0710190000-487f87885e45a61ac64d | View in MoNA |
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