Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:25:59 UTC |
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Update date | 2015-07-21 06:59:08 UTC |
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Primary ID | FDB027531 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | LysoPC(14:1(9Z)) |
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Description | LysoPC(14:1(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(14:1(9Z)), in particular, consists of one chain of myristoleic acid at the C-1 position. The myristoleic acid moiety is derived from milk fats. 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. [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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1-(9Z-Tetradecenoyl)-sn-glycero-3-ocholine | ChEBI | 1-Myristoleoyl-glycero-3-ocholine | ChEBI | 1-myristoleoyl-glycero-3-phosphocholine | hmdb | LPC 14:1(9Z)/0:0 | ChEBI | LPC(14:1(9Z)/0:0) | ChEBI | LPC(14:1) | hmdb | LPC(14:1/0:0) | hmdb | LPC(14:1n5/0:0) | hmdb | LPC(14:1w5/0:0) | hmdb | LyPC(14:1) | hmdb | LyPC(14:1/0:0) | hmdb | LyPC(14:1n5/0:0) | hmdb | LyPC(14:1w5/0:0) | hmdb | Lysoatidylcholine(14:1(9Z)/0:0) | ChEBI | Lysoatidylcholine(14:1) | HMDB | Lysoatidylcholine(14:1/0:0) | HMDB | Lysoatidylcholine(14:1N5/0:0) | HMDB | Lysoatidylcholine(14:1W5/0:0) | HMDB | LysoPC 14:1(9Z)/0:0 | ChEBI | LysoPC(14:1(9Z)/0:0) | ChEBI | LysoPC(14:1) | hmdb | LysoPC(14:1/0:0) | hmdb | LysoPC(14:1n5/0:0) | hmdb | LysoPC(14:1w5/0:0) | hmdb | Lysophosphatidylcholine(14:1) | hmdb | Lysophosphatidylcholine(14:1/0:0) | hmdb | Lysophosphatidylcholine(14:1n5/0:0) | hmdb | Lysophosphatidylcholine(14:1w5/0:0) | hmdb |
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Predicted Properties | |
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Chemical Formula | C22H44NO7P |
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IUPAC name | (2-{[(2R)-2-hydroxy-3-(tetradec-9-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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InChI Identifier | InChI=1S/C22H44NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h8-9,21,24H,5-7,10-20H2,1-4H3/t21-/m1/s1 |
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InChI Key | JXGLGTFMAQOJBB-OAQYLSRUSA-N |
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Isomeric SMILES | [H][C@@](O)(COC(=O)CCCCCCCC=CCCCC)COP([O-])(=O)OCC[N+](C)(C)C |
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Average Molecular Weight | 465.561 |
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Monoisotopic Molecular Weight | 465.285539279 |
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Classification |
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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 | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Not Available |
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External Links |
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ChemSpider ID | 24766524 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C04230 |
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Pubchem Compound ID | 24779456 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB10380 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Lecithin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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60 kDa lysophospholipase | ASPG | Q86U10 | Eosinophil lysophospholipase | CLC | Q05315 | Platelet-activating factor acetylhydrolase | PLA2G7 | Q13093 | Platelet-activating factor acetylhydrolase IB subunit gamma | PAFAH1B3 | Q15102 | Platelet-activating factor acetylhydrolase IB subunit beta | PAFAH1B2 | P68402 | Platelet-activating factor acetylhydrolase 2, cytoplasmic | PAFAH2 | Q99487 | Acyl-protein thioesterase 1 | LYPLA1 | O75608 | Acyl-protein thioesterase 2 | LYPLA2 | O95372 | Phosphatidylcholine-sterol acyltransferase | LCAT | P04180 | Lysophospholipid acyltransferase 5 | LPCAT3 | Q6P1A2 | Lysophosphatidylcholine acyltransferase 2 | LPCAT2 | Q7L5N7 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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