Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H13NO4P.Ca.Cl |
| Molecular Weight | 257.666 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].[Ca++].C[N+](C)(C)CCOP([O-])([O-])=O
InChI
InChIKey=ICVPTJCCKTXCDT-UHFFFAOYSA-L
InChI=1S/C5H14NO4P.Ca.ClH/c1-6(2,3)4-5-10-11(7,8)9;;/h4-5H2,1-3H3,(H-,7,8,9);;1H/q;+2;/p-2
DescriptionCurator's Comment: The description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB01565 | https://www.ncbi.nlm.nih.gov/pubmed/11922473 | https://www.ncbi.nlm.nih.gov/pubmed/10203703 | https://www.ncbi.nlm.nih.gov/pubmed/5808301
Curator's Comment: The description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB01565 | https://www.ncbi.nlm.nih.gov/pubmed/11922473 | https://www.ncbi.nlm.nih.gov/pubmed/10203703 | https://www.ncbi.nlm.nih.gov/pubmed/5808301
Phosphorylcholine (ChoP) is a small zwitterionic amino alcohol, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. Phosphorylcholine is the precursor metabolite of choline in the glycine, serine, and threonine metabolism pathways and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway. Phosphorylcholine is an interesting compound from an immunologic point of view, being an immunodominant determinant of pneumococcal teichoic acids and also a major prerequisite for proinflammatory effects of PAF and PAF-like lipids where PC is a common denominator. PC is also a component of some bacteria, apoptotic cells, and OxLDL, which, if exposed, is immunogenic. PC has several properties that could in principle both promote and protect against disease, depending on the pathogen and type of inflammatory reaction. In the field of interventional cardiology, phosphorylcholine is used as a synthetic polymer-based coating, applied to drug-eluting stents, to prevent the occurrence of coronary artery restenosis. To date, more than 120,000 Phosphorylcholine-coated stents have been implanted in patients with no apparent deleterious effect in the long term compared to bare metal stent technologies
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Natural antibodies with the T15 idiotype may act in atherosclerosis, apoptotic clearance, and protective immunity. | 2000 Jun |
|
| Analysis of plant phosphatidylcholines by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2001 |
|
| Radiotherapeutic response of Ehrlich ascites tumor cells perfused in agarose gel threads and implanted in mice. A 31P MR spectroscopy study. | 2001 Apr |
|
| A new structural type for Haemophilus influenzae lipopolysaccharide. Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 486. | 2001 Apr |
|
| Human in-vivo 31P MR spectroscopy of benign and malignant breast tumors. | 2001 Apr-Jun |
|
| Human C-reactive protein: expression, structure, and function. | 2001 Aug |
|
| The CTP:phosphocholine cytidylyltransferase encoded by the licC gene of Streptococcus pneumoniae: cloning, expression, purification, and characterization. | 2001 Dec 30 |
|
| Purification and kinetic characterization of CTP:phosphocholine cytidylyltransferase from Saccharomyces cerevisiae. | 2001 Feb |
|
| Biosynthesis of phosphatidylcholine from a phosphocholine precursor pool derived from the late endosomal/lysosomal degradation of sphingomyelin. | 2001 Jun 1 |
|
| Protein chemistry at membrane interfaces: non-additivity of electrostatic and hydrophobic interactions. | 2001 Jun 8 |
|
| Immunohistochemical localization and differentiation of phosphocholine-containing antigens of the porcine, parasitic nematode, Ascaris suum. | 2001 Mar |
|
| Synthetic studies on glycosphingolipids from Protostomia phyla: synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. | 2001 Nov |
|
| Fiber-optic luminescent sensors with composite oxygen-sensitive layers and anti-biofouling coatings. | 2001 Nov 1 |
|
| DHEA-PC slows the progression of type 2 diabetes (non-insulin-dependent diabetes mellitus) in the ZDF/Gmi-fa/fa rat. | 2001 Summer |
|
| Inhibition of phosphatidylcholine synthesis is associated with excitotoxic cell death in cerebellar granule cell cultures. | 2002 |
|
| The M603 idiotype is lost in the response to phosphocholine in terminal deoxynucleotidyl transferase-deficient mice. | 2002 Apr |
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| Metabolic changes detected by in vivo magnetic resonance studies of HEPA-1 wild-type tumors and tumors deficient in hypoxia-inducible factor-1beta (HIF-1beta): evidence of an anabolic role for the HIF-1 pathway. | 2002 Feb 1 |
|
| T15-idiotype-negative B cells dominate the phosphocholine binding cells in the preimmune repertoire of T15i knockin mice. | 2002 Feb 1 |
|
| Kinetic analyses of liver phosphatidylcholine and phosphatidylethanolamine biosynthesis using (13)C NMR spectroscopy. | 2002 Feb 28 |
|
| Structure and mechanism of CTP:phosphocholine cytidylyltransferase (LicC) from Streptococcus pneumoniae. | 2002 Feb 8 |
|
| The three-dimensional structure of calcium-depleted human C-reactive protein from perfectly twinned crystals. | 2002 Jun |
|
| Increased choline kinase activity in human breast carcinomas: clinical evidence for a potential novel antitumor strategy. | 2002 Jun 20 |
|
| Interactions of cyclosporines with lipid membranes as studied by solid-state nuclear magnetic resonance spectroscopy and high-sensitivity titration calorimetry. | 2002 Mar |
|
| Melanoma tumors acquire a new phospholipid metabolism phenotype under cystemustine as revealed by high-resolution magic angle spinning proton nuclear magnetic resonance spectroscopy of intact tumor samples. | 2002 Mar 15 |
|
| Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. | 2002 May |
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| Diethanolamine induces hepatic choline deficiency in mice. | 2002 May |
|
| Protein encapsulation in liposomes: efficiency depends on interactions between protein and phospholipid bilayer. | 2002 May 10 |
|
| Choline transport in Leishmania major promastigotes and its inhibition by choline and phosphocholine analogs. | 2002 Nov-Dec |
|
| Quantitation of choline and its metabolites in tissues and foods by liquid chromatography/electrospray ionization-isotope dilution mass spectrometry. | 2002 Sep 15 |
|
| Phosphorylation of Saccharomyces cerevisiae choline kinase on Ser30 and Ser85 by protein kinase A regulates phosphatidylcholine synthesis by the CDP-choline pathway. | 2002 Sep 20 |
|
| Quantitative detection of C-reactive protein using phosphocholine-labelled enzyme or microspheres. | 2003 Jan 15 |
|
| Biosynthesis of phosphatidylcholine in bacteria. | 2003 Mar |
Patents
Sample Use Guides
Male Wistar rats were treated with Phosphorylcholine, 200mg/kg as single IV injection.
Route of Administration:
Intravenous
Red blood cells from BALB/c mice (MRBC) were either conjugated with PC (Phosphorylcholine), 2,4,6-trinitrophenyl (TNP) or treated with phospholipase A2 (PLA2) to expose PC on the cell membrane (determined by hemagglutination with the anti-PC myeloma HOPC8). When BALB/c mice were immunized i.v. with the conjugated or enzyme-treated MRBC, a significant polyclonal antibody response occurred (p less than 0.05) using PC-MRBC or PLA2-treated MRBC, but not with TNP-MRBC or sham-treated MRBC. No anti-PC or anti-MRBC immunoglobulin-secreting cells developed after immunization. Repeated immunization with PC-MRBC resulted in similar levels of protein A PFC after each immunization but no anti-PC, anti-MRBC or anti-PC-MRBC PFC.
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15557-11-6
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100000079440
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m8744
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DTXSID601335812
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SUB14856MIG
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ACTIVE MOIETY
SUBSTANCE RECORD
