| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2008-09-16 13:20:00 UTC |
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| Update Date | 2019-01-11 19:27:57 UTC |
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| HMDB ID | HMDB0010386 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | LysoPC(18:2(9Z,12Z)) |
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| Description | LysoPC(18:2(9Z,12Z)) 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(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. 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,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholine | ChEBI | | 1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholine | ChEBI | | 1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholine | ChEBI | | 1-18:2-LysoPC | ChEBI | | 1-Linoleoyl-glycero-3-phosphocholine | ChEBI | | 1-Linoleoylglycerophosphocholine | ChEBI | | LPC 18:2(9Z,12Z)/0:0 | ChEBI | | LPC(18:2) | ChEBI | | LPC(18:2/0:0) | ChEBI | | LPC(18:2n6/0:0) | ChEBI | | LPC(18:2Omega6/0:0) | ChEBI | | LyPC(18:2) | ChEBI | | LyPC(18:2n6/0:0) | ChEBI | | LyPC(18:2omega6/0:0) | ChEBI | | LysoPC 18:2(9Z,12Z)/0:0 | ChEBI | | LysoPC(18:2(9Z,12Z)/0:0) | ChEBI | | LysoPC(18:2) | ChEBI | | LysoPC(18:2/0:0) | ChEBI | | LysoPC(18:2n6/0:0) | ChEBI | | LysoPC(18:2omega6/0:0) | ChEBI | | Lysophosphatidylcholine(18:2(9Z,12Z)/0:0) | ChEBI | | Lysophosphatidylcholine(18:2) | ChEBI | | Lysophosphatidylcholine(18:2/0:0) | ChEBI | | Lysophosphatidylcholine(18:2n6/0:0) | ChEBI | | Lysophosphatidylcholine(18:2omega6/0:0) | ChEBI | | PC 18:2(9Z,12Z)/0:0 | ChEBI | | PC(18:2(9Z,12Z)/0:0) | ChEBI | | LyPC(18:2/0:0) | Lipid Annotator | | LysoPC(18:2(9Z,12Z)) | Lipid Annotator |
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| Chemical Formula | C26H50NO7P |
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| Average Molecular Weight | 519.6515 |
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| Monoisotopic Molecular Weight | 519.332489471 |
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| IUPAC Name | (2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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| Traditional Name | (2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C |
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| InChI Identifier | InChI=1S/C26H50NO7P/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/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1 |
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| InChI Key | SPJFYYJXNPEZDW-FTJOPAKQSA-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: Health 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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| Disease References | | Schizophrenia |
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- Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
| | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| | Obesity |
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- Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ]
- Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
| | Cirrhosis |
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- Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
| | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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