Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:25 UTC |
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Updated at | 2022-03-10 22:21:37 UTC |
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NP-MRD ID | NP0044310 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | LysoPC(16:0/0:0) |
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Description | LysoPC(16:0/0:0) Is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(16:0/0:0), In particular, consists of one hexadecanoyl chain. 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. LysoPC(16:0/0:0) Is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1 |
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Synonyms | Value | Source |
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(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate | ChEBI | 1-16:0-LysoPC | ChEBI | 1-16:0-Lysophosphatidylcholine | ChEBI | 1-Hexadecanoyl-2-lysophosphatidylcholine | ChEBI | 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine | ChEBI | 1-Palmitoyl-2-lysophosphatidylcholine | ChEBI | 1-Palmitoyl-GPC | ChEBI | 1-Palmitoyl-GPC (16:0) | ChEBI | 1-Palmitoyl-phosphatidylcholine | ChEBI | 1-Palmitoyl-sn-glycero-3-phosphocholine | ChEBI | 1-Palmitoylphosphatidylcholine | ChEBI | 16:0 LYSO-PC | ChEBI | GPC(16:0) | ChEBI | GPC(16:0/0:0) | ChEBI | GPCho 16:0/0:0 | ChEBI | GPCho(16:0/0:0) | ChEBI | LPC 16:0/0:0 | ChEBI | LPC(16:0) | ChEBI | LPC(16:0/0:0) | ChEBI | LyPC(16:0) | ChEBI | LyPC(16:0/0:0) | ChEBI | LysoPC 16:0/0:0 | ChEBI | LysoPC(16:0) | ChEBI | Lysophosphatidylcholine(16:0) | ChEBI | Lysophosphatidylcholine(16:0/0:0) | ChEBI | PC(16:0/0:0) | ChEBI | (2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid | Generator | 1-Palmitoyl-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-lysophosphatidylcholine | HMDB | LysoPC a C16:0 | HMDB | 1-Pam-2-lysoptdcho | HMDB | 1-Hexadecanoyl-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-sn-glycerol-3-phosphorylcholine | HMDB | 1-Palmitoylglycerol-3-phosphorylcholine | HMDB | Hydroxide inner salt(S)-isomer OF we 201 | HMDB | 1-O-Hexadecylpropanediol 3-phosphorylcholine | HMDB | 1-Palmitoyllysophosphatidylcholine | HMDB | LYSO-PC | HMDB | Hydroxide inner salt(R)-isomer OF we 201 | HMDB | Hydroxide inner salt(+-)-isomer OF we 201 | HMDB | Palmitoyl lysophosphatidylcholine | HMDB | 1-Hexadecanoylglycerophosphocholine | HMDB | 1-Palmitoylglycerophosphocholine | HMDB | 1-Hexadecanoyl-sn-glycero-3-phosphocholine | HMDB | 1-Hexadecanoyl-sn-glycerol-3-phosphorylcholine | HMDB | 1-Hexadecanoyllysolecithin | HMDB | 1-Hexadecyl-sn-glycero-3-phosphocholine | HMDB | 1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine | HMDB | 1-O-Palmitoyl-sn-glycero-3-phosphocholine | HMDB | 1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholine | HMDB | 1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-L-alpha-lysophosphatidylcholine | HMDB | 1-Palmitoyl-L-α-lysophosphatidylcholine | HMDB | 1-Palmitoyl-sn-glycero-3-phosphorylcholine | HMDB | 1-Palmitoyl-sn-glycerol-3-phosphatidylcholine | HMDB | 1-Palmitoyl-sn-glycerol-3-phosphocholine | HMDB | 1-Palmitoyllecithin | HMDB | C(16)-Lysophosphatidylcholine | HMDB | L-Palmitoyllysolecithin | HMDB | L-alpha-Lysopalmitoylphosphatidylcholine | HMDB | L-alpha-Palmitoyllysophosphatidylcholine | HMDB | L-Α-lysopalmitoylphosphatidylcholine | HMDB | L-Α-palmitoyllysophosphatidylcholine | HMDB | Lysophosphatidylcholine C16:0 | HMDB | MPPC | HMDB | Palmitoyl L-alpha-lysolecithin | HMDB | Palmitoyl L-alpha-lysophosphatidylcholine | HMDB | Palmitoyl L-lysophosphatidylcholine | HMDB | Palmitoyl L-α-lysolecithin | HMDB | Palmitoyl L-α-lysophosphatidylcholine | HMDB | gamma-Palmitoyl-L-alpha-lysophosphatidylcholine | HMDB | Γ-palmitoyl-L-α-lysophosphatidylcholine | HMDB | 1-Hexadecanoyl-3-glycerophosphorylcholine | HMDB | 1-Palmitoyl-3-glycerylphosphorylcholine | HMDB | 1-Palmitoyllysolecithin | HMDB | Palmitoyllysolecithin | HMDB | Palmitoyllysophosphatidyl choline | HMDB | LysoPC(16:0/0:0) | Lipid Annotator, ChEBI |
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Chemical Formula | C24H50NO7P |
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Average Mass | 495.6301 Da |
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Monoisotopic Mass | 495.33249 Da |
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IUPAC Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | 17364-16-8 |
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SMILES | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C |
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InChI Identifier | InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1 |
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InChI Key | ASWBNKHCZGQVJV-HSZRJFAPSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. |
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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 | 1-acyl-sn-glycero-3-phosphocholines |
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Alternative Parents | |
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Substituents | - 1-acyl-sn-glycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Organic oxygen compound
- Organopnictogen compound
- Carbonyl group
- Organic salt
- Amine
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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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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