You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2006-05-22 15:12:12 UTC |
---|
Update Date | 2020-02-27 16:50:54 UTC |
---|
HMDB ID | HMDB0002815 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | LysoPC(18:1(9Z)/0:0) |
---|
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. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
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 | ChEBI | LPC 18:1(9Z)/0:0 | ChEBI | LPC(18:1(9Z)/0:0) | ChEBI | LysoPC 18:1(9Z)/0:0 | ChEBI | Lysophosphatidylcholine 18:1 | ChEBI | Lysophosphatidylcholine(18:1(9Z)/0:0) | ChEBI | PC 18:1(9Z)/0:0 | ChEBI | PC(18:1(9Z)/0:0) | ChEBI | 1-Oleoyl-glycero-3-phosphocholine | HMDB | LysoPC(18:1/0:0) | HMDB | LysoPC(18:1(9Z)) | HMDB | Lysophosphatidylcholine(18:1) | HMDB | LysoPC(18:1) | HMDB | LyPC(18:1/0:0) | HMDB | LyPC(18:1) | HMDB | LPC(18:1/0:0) | HMDB | LPC(18:1) | HMDB | 1-(9Z-Octadecenoyl)-glycero-3-phosphocholine | HMDB | Lysophosphatidylcholine(18:1/0:0) | HMDB | 1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine | HMDB | 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(18:1W9/0:0) | HMDB | LysoPC a C18:1 | HMDB | LysoPC(18:1n9/0:0) | HMDB | LysoPC(18:1W9/0:0) | 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 | HMDB | 1-OGPC | HMDB | 1-Oleoyl lysophosphatidylcholine | HMDB | 1-Oleoyl-lysopc | HMDB | 1-O-Oleoyl-sn-glycero-3-phosphocholine | HMDB | 1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine | HMDB | 1-Oleoyl-GPC | HMDB | 1-Oleoyl-lysophosphatidylcholine | HMDB | 1-Oleoyl-sn-glycerol-3-phosphatidylcholine | HMDB | 1-Oleoyl-sn-glycerol-3-phosphorylcholine | HMDB | GPC(18:1(9Z)) | HMDB | GPC(18:1(9Z)/0:0) | HMDB | GPC(18:1) | HMDB | GPC(18:1n9) | HMDB | GPC(18:1n9/0:0) | HMDB | GPC(18:1W9) | HMDB | GPC(18:1W9/0:0) | HMDB | LPC(18:1(9Z)) | HMDB | LPC(18:1n9) | HMDB | LPC(18:1W9) | HMDB | LysoPC(18:1n9) | HMDB | LysoPC(18:1W9) | HMDB | Lysophosphatidylcholine C18:1 | HMDB | Lysophosphatidylcholine(18:1(9Z)) | HMDB | Lysophosphatidylcholine(18:1n9) | HMDB | Lysophosphatidylcholine(18:1W9) | HMDB | LysoPC(18:1(9Z)/0:0) | ChEBI |
|
---|
Chemical Formula | C26H52NO7P |
---|
Average Molecular Weight | 521.6673 |
---|
Monoisotopic Molecular Weight | 521.348139535 |
---|
IUPAC Name | (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
---|
Traditional Name | (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
---|
CAS Registry Number | 19420-56-5 |
---|
SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C |
---|
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 |
---|
InChI Key | YAMUFBLWGFFICM-PTGWMXDISA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphocholines |
---|
Direct Parent | 1-acyl-sn-glycero-3-phosphocholines |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Organoleptic effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-024u-9431010000-8c34065bb1a9ce8460a8 | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 31.5 +/- 10.4 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 37.47 +/- 7.73 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 11.7 (9.93-13.5) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 23.83(5.62) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 17.5 +/- 4.62 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 16.4 (13.4-21.2) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 17.13 +/- 4.59 uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 37.465 +/- 7.733 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 4.9 +/- 5.49 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 6.59 +/- 9.25 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0-0.2 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 0.02(0.0-0.24) umol/mmol creatinine | Newborn (0-30 days old) | Female | Normal | | details | Urine | Detected and Quantified | 0.01(0.0-0.05) umol/mmol creatinine | Newborn (0-30 days old) | Male | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 13.5 +/- 5.2 uM | Children (1-13 years old) | Both | Obese | | details | Blood | Detected and Quantified | 12.7 +/- 5.8 uM | Children (1-13 years old) | Both | Obese | | details | Blood | Detected and Quantified | 12.3 +/- 5.2 uM | Children (1-13 years old) | Both | Obese | | details | Blood | Detected and Quantified | 12.7 +/- -5.5 uM | Children (1-13 years old) | Both | Obese | | details | Blood | Detected and Quantified | 21.15(5.32) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 13.380 (12.740) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 27.946 (9.468) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 12.73 +/- 3.96 uM | Children (1-13 years old) | Both | Obese | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | liver cirrhosis | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Pregnancy |
---|
- 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 |
---|
- 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 |
---|
- 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 ]
| Colorectal cancer |
---|
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
|
|
---|
Associated OMIM IDs | |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB005287 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 17240641 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 16081932 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 28610 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | PCHOLOLE_HS |
---|
MarkerDB ID | |
---|
References |
---|
Synthesis Reference | Chung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
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 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
|
---|