lysophosphatidylcholine   

GtoPdb Ligand ID: 2508

Abbreviated name: LPC
Comment: The structure shown here is a representative example of the lysophosphatidylcholine class of compounds. The R group terminal linked to the ester (shown here as a methyl group) is a fatty acid chain of varying length. For examples of lysophospatidylcholine compounds with specified chain lengths see oleoyl-lysophosphatidylcholine and 1-palmitoyl-lysophosphatidylcholine.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 114.93
Molecular weight 299.11
XLogP -2.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(COP(=O)(OCC[N+](C)(C)C)[O-])COC(=O)C
Isomeric SMILES O[C@@H](COP(=O)(OCC[N+](C)(C)C)[O-])COC(=O)C
InChI InChI=1S/C10H22NO7P/c1-9(12)16-7-10(13)8-18-19(14,15)17-6-5-11(2,3)4/h10,13H,5-8H2,1-4H3/t10-/m1/s1
InChI Key RYCNUMLMNKHWPZ-SNVBAGLBSA-N
References
1. Clair T, Aoki J, Koh E, Bandle RW, Nam SW, Ptaszynska MM, Mills GB, Schiffmann E, Liotta LA, Stracke ML. (2003)
Autotaxin hydrolyzes sphingosylphosphorylcholine to produce the regulator of migration, sphingosine-1-phosphate.
Cancer Res., 63 (17): 5446-53. [PMID:14500380]
2. Davenport AP, Alexander SP, Sharman JL, Pawson AJ, Benson HE, Monaghan AE, Liew WC, Mpamhanga CP, Bonner TI, Neubig RR et al.. (2013)
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands.
Pharmacol. Rev., 65 (3): 967-86. [PMID:23686350]
3. Kabarowski JH, Zhu K, Le LQ, Witte ON, Xu Y. (2001)
Lysophosphatidylcholine as a ligand for the immunoregulatory receptor G2A.
Science, 293 (5530): 702-5. [PMID:11474113]
4. Lesage F, Terrenoire C, Romey G, Lazdunski M. (2000)
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
J. Biol. Chem., 275 (37): 28398-405. [PMID:10880510]
5. Mihara H, Boudaka A, Shibasaki K, Yamanaka A, Sugiyama T, Tominaga M. (2010)
Involvement of TRPV2 activation in intestinal movement through nitric oxide production in mice.
J. Neurosci., 30 (49): 16536-44. [PMID:21147993]
6. Monet M, Gkika D, Lehen'kyi V, Pourtier A, Vanden Abeele F, Bidaux G, Juvin V, Rassendren F, Humez S, Prevarsakaya N. (2009)
Lysophospholipids stimulate prostate cancer cell migration via TRPV2 channel activation.
Biochim. Biophys. Acta, 1793 (3): 528-39. [PMID:19321128]
7. No authors listed. (2005)
Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4. (Retraction).
J. Biol. Chem., 280 (52): 43280. [PMID:16498716]
8. Seuwen K, Ludwig MG, Wolf RM. (2006)
Receptors for protons or lipid messengers or both?.
J. Recept. Signal Transduct. Res., 26 (5-6): 599-610. [PMID:17118800]
9. Tobo A, Tobo M, Nakakura T, Ebara M, Tomura H, Mogi C, Im DS, Murata N, Kuwabara A, Ito S et al.. (2015)
Characterization of Imidazopyridine Compounds as Negative Allosteric Modulators of Proton-Sensing GPR4 in Extracellular Acidification-Induced Responses.
PLoS ONE, 10 (6): e0129334. [PMID:26070068]
10. Witte ON, Kabarowski JH, Xu Y, Le LQ, Zhu K. (2005)
Retraction.
Science, 307 (5707): 206. [PMID:15653487]
11. Yang LV, Radu CG, Roy M, Lee S, McLaughlin J, Teitell MA, Iruela-Arispe ML, Witte ON. (2007)
Vascular abnormalities in mice deficient for the G protein-coupled receptor GPR4 that functions as a pH sensor.
Mol. Cell. Biol., 27 (4): 1334-47. [PMID:17145776]
12. Zhu K, Baudhuin LM, Hong G, Williams FS, Cristina KL, Kabarowski JH, Witte ON, Xu Y. (2001)
Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4.
J. Biol. Chem., 276 (44): 41325-35. [PMID:11535583]