2-oleoyl-LPA   Click here for help

GtoPdb Ligand ID: 2936

Synonyms: 2-acyl-1LPA | 2Acyl-LPA
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 21
Topological polar surface area 123.1
Molecular weight 436.26
XLogP 5.9
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCC=CCCCCCCCC(=O)OC(COP(=O)(O)O)CO
Isomeric SMILES CCCCCCCC/C=C\CCCCCCCC(=O)OC(COP(=O)(O)O)CO
InChI InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-
InChI Key ZOOLJLSXNRZLDH-KTKRTIGZSA-N
References
1. Bandoh K, Aoki J, Taira A, Tsujimoto M, Arai H, Inoue K. (2000)
Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species. Structure-activity relationship of cloned LPA receptors.
FEBS Lett, 478 (1-2): 159-65. [PMID:10922489]
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. Divorty N, Mackenzie AE, Nicklin SA, Milligan G. (2015)
G protein-coupled receptor 35: an emerging target in inflammatory and cardiovascular disease.
Front Pharmacol, 6: 41. [PMID:25805994]
4. Kuc D, Zgrajka W, Parada-Turska J, Urbanik-Sypniewska T, Turski WA. (2008)
Micromolar concentration of kynurenic acid in rat small intestine.
Amino Acids, 35 (2): 503-5. [PMID:18235993]
5. Oka S, Ota R, Shima M, Yamashita A, Sugiura T. (2010)
GPR35 is a novel lysophosphatidic acid receptor.
Biochem Biophys Res Commun, 395 (2): 232-7. [PMID:20361937]
6. Southern C, Cook JM, Neetoo-Isseljee Z, Taylor DL, Kettleborough CA, Merritt A, Bassoni DL, Raab WJ, Quinn E, Wehrman TS et al.. (2013)
Screening β-Arrestin Recruitment for the Identification of Natural Ligands for Orphan G-Protein-Coupled Receptors.
J Biomol Screen, 18 (5): 599-609. [PMID:23396314]
7. Taniguchi Y, Tonai-Kachi H, Shinjo K. (2006)
Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35.
FEBS Lett, 580 (21): 5003-8. [PMID:16934253]
8. Zhao P, Sharir H, Kapur A, Cowan A, Geller EB, Adler MW, Seltzman HH, Reggio PH, Heynen-Genel S, Sauer M, Chung TD, Bai Y, Chen W, Caron MG, Barak LS, Abood ME. (2010)
Targeting of the orphan receptor GPR35 by pamoic acid: a potent activator of extracellular signal-regulated kinase and β-arrestin2 with antinociceptive activity.
Mol Pharmacol, 78 (4): 560-8. [PMID:20826425]