pamoic acid   Click here for help

GtoPdb Ligand ID: 2920

Synonyms: embonic acid
Compound class: Synthetic organic
Comment: Many salts and esters or pamoates are commecially available and are often used in bio-assays in place of pamoic acid.

Although not an approved drug itself, pamoic acid is a component of the INN-assigned compounds listed above.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 115.06
Molecular weight 388.09
XLogP 5.58
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES OC(=O)c1cc2ccccc2c(c1O)Cc1c(O)c(cc2c1cccc2)C(=O)O
Isomeric SMILES OC(=O)c1cc2ccccc2c(c1O)Cc1c(O)c(cc2c1cccc2)C(=O)O
InChI InChI=1S/C23H16O6/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h1-10,24-25H,11H2,(H,26,27)(H,28,29)
InChI Key WLJNZVDCPSBLRP-UHFFFAOYSA-N
References
1. 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]
2. 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]
3. Jenkins L, Brea J, Smith NJ, Hudson BD, Reilly G, Bryant NJ, Castro M, Loza MI, Milligan G. (2010)
Identification of novel species-selective agonists of the G-protein-coupled receptor GPR35 that promote recruitment of β-arrestin-2 and activate Gα13.
Biochem J, 432 (3): 451-9. [PMID:20919992]
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]