| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-05-22 15:12:12 UTC |
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| Update Date | 2018-04-16 17:00:53 UTC |
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| HMDB ID | HMDB0002815 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | LysoPC(18:1(9Z)) |
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| Description | LysoPC(18:1(9Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. 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(18:19Z)), in particular, consists of one chain of oleic acid at the C-1 position. The oleic acid moiety, an omega-9 fatty acid, is derived from various animal and vegetable sources such as olive oil, acai and grapeseed oil. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine | ChEBI | | 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine | ChEBI | | 1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine | ChEBI | | 1-Oleoyl-sn-glycero-3-phosphorylcholine | ChEBI | | 1-Oleoylglycerophosphocholine | ChEBI | | 3-Oleoyl-rac-glycerol-1-phosphorylcholine | ChEBI | | LPC 18:1(9Z)/0:0 | ChEBI | | LPC(18:1(9Z)/0:0) | ChEBI | | LysoPC 18:1(9Z)/0:0 | ChEBI | | LysoPC(18:1(9Z)/0:0) | ChEBI | | Lysophosphatidylcholine(18:1(9Z)/0:0) | ChEBI | | PC 18:1(9Z)/0:0 | ChEBI | | PC(18:1(9Z)/0:0) | ChEBI | | 1-Oleoyl-sn-glycero-3-phosphocholine | HMDB | | Choline phosphate (ester) 3-ester with 1-monoolein | HMDB | | Choline phosphate 3-ester with 1-monoolein | HMDB | | gpcho(18:1(9Z)/0:0)[rac] | HMDB | | LPC(18:1n9/0:0) | HMDB | | LPC(18:1W9/0:0) | HMDB | | LyPC(18:1) | HMDB | | LyPC(18:1/0:0) | HMDB | | LyPC(18:1W9/0:0) | HMDB | | LysoPC a C18:1 | HMDB | | LysoPC(18:1) | HMDB | | LysoPC(18:1n9/0:0) | HMDB | | LysoPC(18:1W9/0:0) | HMDB | | Lysophosphatidylcholine(18:1) | HMDB | | Lysophosphatidylcholine(18:1/0:0) | HMDB | | Lysophosphatidylcholine(18:1n9/0:0) | HMDB | | Lysophosphatidylcholine(18:1W9/0:0) | HMDB | | LysoPIC(18:1/0:0) | HMDB | | Olein-1-mono-3-phosphate ester with choline | HMDB | | Oleoyl lysolecithin | HMDB | | Oleoyl lysophosphatidylcholine | HMDB | | 1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholine | MeSH | | 1-OGPC | MeSH | | 1-Oleoyl lysophosphatidylcholine | MeSH | | 1-Oleoyl-lysopc | MeSH | | 1-(9Z-octadecenoyl)-glycero-3-phosphocholine; Lysophosphatidylcholine(18:1/0:0) | Lipid Annotator | | 1-oleoyl-glycero-3-phosphocholine | Lipid Annotator | | LysoPC(18:1/0:0) | Lipid Annotator | | LysoPC(18:1(9Z)) | Lipid Annotator | | LPC(18:1/0:0) | Lipid Annotator | | LPC(18:1) | Lipid Annotator | | 1-(9Z-octadecenoyl)-glycero-3-phosphocholine | Lipid Annotator |
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| Chemical Formula | C26H52NO7P |
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| Average Molecular Weight | 521.6673 |
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| Monoisotopic Molecular Weight | 521.348139535 |
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| IUPAC Name | (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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| Traditional Name | (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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| CAS Registry Number | 3542-29-8 |
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| SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C |
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| InChI Identifier | InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1 |
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| InChI Key | YAMUFBLWGFFICM-PTGWMXDISA-N |
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| Chemical Taxonomy |
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| Description | This compound 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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| Ontology |
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| Physiological effect | Organoleptic effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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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 | |
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| General References | - Frasch SC, Zemski-Berry K, Murphy RC, Borregaard N, Henson PM, Bratton DL: Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A. J Immunol. 2007 May 15;178(10):6540-8. [PubMed:17475884 ]
- Yang J, Zhao X, Liu X, Wang C, Gao P, Wang J, Li L, Gu J, Yang S, Xu G: High performance liquid chromatography-mass spectrometry for metabonomics: potential biomarkers for acute deterioration of liver function in chronic hepatitis B. J Proteome Res. 2006 Mar;5(3):554-61. [PubMed:16512670 ]
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