PHOSPHORYLCHOLINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H14NO4P
Molecular Weight	183.1427
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCOP(O)([O-])=O

InChI

InChIKey=YHHSONZFOIEMCP-UHFFFAOYSA-N

InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8414498
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Choline-phosphate cytidylyltransferase A 3 Target ID: P49585 Gene ID: 5130.0 Gene Symbol: PCYT1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/238177	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Dominant cross-reactive antibodies generated during the response to a variety of oral bacterial species detect phosphorylcholine.	1999 Jan	10065949
Natural antibodies with the T15 idiotype may act in atherosclerosis, apoptotic clearance, and protective immunity.	2000 Jun	10862788
A new structural type for Haemophilus influenzae lipopolysaccharide. Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 486.	2001 Apr	11277939
Human C-reactive protein: expression, structure, and function.	2001 Aug	11532280
Quantitative analysis and molecular species fingerprinting of triacylglyceride molecular species directly from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry.	2001 Aug 1	11476549
The CTP:phosphocholine cytidylyltransferase encoded by the licC gene of Streptococcus pneumoniae: cloning, expression, purification, and characterization.	2001 Dec 30	11786295
Glycosylated molecular variants of C-reactive proteins from the major carp Catla catla in fresh and polluted aquatic environments.	2001 Jul	12151716
Characterization of two monoclonal antibodies raised in Btk(xid) mice that recognize phosphorylcholine-bearing antigens from Trichinella and other helminths.	2001 Jun	11412384
Protein chemistry at membrane interfaces: non-additivity of electrostatic and hydrophobic interactions.	2001 Jun 8	11397078
Immunohistochemical localization and differentiation of phosphocholine-containing antigens of the porcine, parasitic nematode, Ascaris suum.	2001 Mar	11289072
Imidazoline I(1) receptor-induced activation of phosphatidylcholine-specific phospholipase C elicits mitogen-activated protein kinase phosphorylation in PC12 cells.	2001 Mar	11274989
Detection of increased choline compounds with proton nuclear magnetic resonance spectroscopy subsequent to malignant transformation of human prostatic epithelial cells.	2001 May 1	11325827
The phosphocholine motif in membranes of Mycoplasma fermentans strains.	2001 May 15	11356581
Synthetic studies on glycosphingolipids from Protostomia phyla: synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi.	2001 Nov	11724239
Phospholipids modulate the substrate specificity of soluble UDP-glucose:steroid glucosyltransferase from eggplant leaves.	2001 Nov	11672729
Fiber-optic luminescent sensors with composite oxygen-sensitive layers and anti-biofouling coatings.	2001 Nov 1	11721912
Structural analysis of the lipopolysaccharide from the nontypable Haemophilus influenzae strain SB 33.	2001 Oct	11606189
[Brain tumors: interest of magnetic resonance spectroscopy for the diagnosis and the prognosis].	2001 Sep	11677409
An improved method for assaying phosphocholine and glycerophosphocholine in mouse tissue.	2001 Sep-Oct	12481847
Inhibition of phosphatidylcholine synthesis is associated with excitotoxic cell death in cerebellar granule cell cultures.	2002	12373513
The M603 idiotype is lost in the response to phosphocholine in terminal deoxynucleotidyl transferase-deficient mice.	2002 Apr	11932921
Metabolic markers of breast cancer: enhanced choline metabolism and reduced choline-ether-phospholipid synthesis.	2002 Apr 1	11929812
Transbilayer movement of fluorescent phospholipid analogues in the cytoplasmic membrane of Escherichia coli.	2002 Apr 30	11969421
In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels.	2002 Aug	12203225
Identification of cellular sections with imaging mass spectrometry following freeze fracture.	2002 Aug 15	12199569
T15-idiotype-negative B cells dominate the phosphocholine binding cells in the preimmune repertoire of T15i knockin mice.	2002 Feb 1	11801665
A calorimetric study of phosphocholine membranes mixed with desmopressin and its diacylated prodrug derivative (DPP).	2002 Feb 21	11897424
Kinetic analyses of liver phosphatidylcholine and phosphatidylethanolamine biosynthesis using (13)C NMR spectroscopy.	2002 Feb 28	11880242
Structure-activity relationships of alkylphosphocholine derivatives: antineoplastic action on brain tumor cell lines in vitro.	2002 Jul	12111115
NMR and pattern recognition studies on liver extracts and intact livers from rats treated with alpha-naphthylisothiocyanate.	2002 Jul 1	12106607
Increased choline kinase activity in human breast carcinomas: clinical evidence for a potential novel antitumor strategy.	2002 Jun 20	12082619
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	11912170
Diethanolamine induces hepatic choline deficiency in mice.	2002 May	11961214
Protein encapsulation in liposomes: efficiency depends on interactions between protein and phospholipid bilayer.	2002 May 10	12003642
Real-time changes in 1H and 31P NMR spectra of malignant human mammary epithelial cells during treatment with the anti-inflammatory agent indomethacin.	2002 Nov	12417996
Evolution of catalytic antibody repertoire in autoimmune mice.	2002 Nov 1	12379363
Binding of C-reactive protein to modified low-density-lipoprotein particles: identification of cholesterol as a novel ligand for C-reactive protein.	2002 Oct 15	12102655
Rapid transbilayer movement of the fluorescent sterol dehydroergosterol in lipid membranes.	2002 Sep	12202377
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	12105205
In vivo and in vitro MR spectroscopic profile of central neurocytomas.	2003 Feb	12541233
Quantitative detection of C-reactive protein using phosphocholine-labelled enzyme or microspheres.	2003 Jan 15	12531203
Choline head groups stabilize the matrix loop regions of the ATP/ADP carrier ScAAC2.	2003 Jan 3	12480522
Biosynthesis of phosphatidylcholine in bacteria.	2003 Mar	12547654
Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline.	2003 Mar 15	12466019

Patents

Sample Use Guides

In Vivo Use Guide

Male Wistar rats were treated with Phosphorylcholine, 200mg/kg as single IV injection.

Route of Administration: Intravenous

In Vitro Use Guide

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.

Name

Type

Language

PHOSPHORYLCHOLINE

Systematic Name

English

Phosphorylcholine [WHO-DD]

Common Name

English

2-(TRIMETHYLAMMONIO)ETHYL HYDROGEN PHOSPHATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

135437