4-{[3-carboxy-2-hydroxy(2H5)naphthalen-1-yl]methyl}-3-hydroxy(2H5)naphthalene-2-carboxylic acid

• ChemBase ID: 176216
• Molecular Formular: C23H16O6
• Molecular Mass: 388.36954
• Monoisotopic Mass: 388.09468823
• SMILES: c1cccc2c1cc(c(c2Cc1c2c(cc(c1O)C(=O)O)cccc2)O)C(=O)O
• Canonical 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)
• InChIKey: WLJNZVDCPSBLRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[3-carboxy-2-hydroxy(^2H₅)naphthalen-1-yl]methyl}-3-hydroxy(^2H₅)naphthalene-2-carboxylic acid
• IUPAC Traditional name: 4-{[3-carboxy-2-hydroxy(^2H₅)naphthalen-1-yl]methyl}-3-hydroxy(^2H₅)naphthalene-2-carboxylic acid
• Synonyms: 4,4'-Methylenebis[3-hydroxy-2-naphthalenecarboxylic Acid; 2,2'-Dihydroxy-1,1'-dinaphthylmethane-3,3'-dicarboxylic Acid; 4,4'-Methylenebis[3-hydroxy-2-naphthoic Acid]; Embonic Acid; KG 122; NSC 30188; NSC 40132; Pamoic Acid-d10

Database IDs

• PubChem SID: 164232126
• PubChem CID: 57369373

CALCULATED PROPERTIES

• Acid pKa: 2.3815763
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.5700001
• LogD (pH = 7.4): -0.95232564
• Log P: 6.0520287
• Molar Refractivity: 107.1698 cm^3
• Polarizability: 42.597775 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P173502

Labelled Pamoic Acid. Agonist of the orphan G protein-coupled receptor GPR35: a potent activator of extracellular signal-regulated kinase and β-arrestin2 with antinociceptive activity. Used as an inhibitor in the real-time fluorescence enzymatic character

REFERENCES

• Fonge H., et al.: Bioconjugate Chem., 18, 1924 (2007)
• Mayr, G.W., et al.: J. Biol. Chem., 282, 35424 (2007)
• Zhao, P. et al.: Mol. Pharmacol., 78, 560 (2007)
• Dorjsujen, D. et al.: Nuc. Acids Res., 37, e128 (2007)