(1R,3R)-1-(3-{[4-(2-fluorophenyl)(2H8)piperazin-1-yl]methyl}-4-methoxyphenyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

• ChemBase ID: 175054
• Molecular Formular: C30H31FN4O3
• Molecular Mass: 514.5905432
• Monoisotopic Mass: 514.23801909
• SMILES: c1cccc(c1F)N1CCN(CC1)Cc1cc(ccc1OC)[C@H]1N[C@H](Cc2c1[nH]c1c2cccc1)C(=O)O
• Canonical SMILES: COc1ccc(cc1CN1CCN(CC1)c1ccccc1F)[C@H]1N[C@H](Cc2c1[nH]c1c2cccc1)C(=O)O
• InChI: InChI=1S/C30H31FN4O3/c1-38-27-11-10-19(16-20(27)18-34-12-14-35(15-13-34)26-9-5-3-7-23(26)31)28-29-22(17-25(33-28)30(36)37)21-6-2-4-8-24(21)32-29/h2-11,16,25,28,32-33H,12-15,17-18H2,1H3,(H,36,37)/t25-,28-/m1/s1
• InChIKey: FUHCEERDBRGPQZ-LEAFIULHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R)-1-(3-{[4-(2-fluorophenyl)(^2H₈)piperazin-1-yl]methyl}-4-methoxyphenyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
• IUPAC Traditional name: (1R,3R)-1-(3-{[4-(2-fluorophenyl)(^2H₈)piperazin-1-yl]methyl}-4-methoxyphenyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
• Synonyms: (1R,3S)-1-[3-[[4-(2-Fluorophenyl)-1-(piperazinyl-d8)]methyl]-4-methoxyphenyl]-2,3,4,9-tetrahydro-1H-Pyrido[3,4-b]indole-3-carboxylic Acid; trans-Ned-19-d8

Database IDs

• PubChem SID: 164230964
• PubChem CID: 71750975

CALCULATED PROPERTIES

• Acid pKa: 1.4880735
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.0752677
• LogD (pH = 7.4): 2.143146
• Log P: 2.0797968
• Molar Refractivity: 145.4632 cm^3
• Polarizability: 56.693993 Å^3
• Polar Surface Area: 80.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N388752

Labelled trans-Ned-19, a cell permeable and potent nicotinic acid adenine dinucleotide phosphate (NAADP) antagonist. trans-Ned-19 inhibits NAADP-mediated Ca2+ release (IC50 = 6 nM) and also inhibits [32P]NAADP binding (IC50 = 0.4 nM). trans-Ned-19 can be

REFERENCES

• Rosen, D. et al.: J. Biol. Chem., 284, 34930 (2009)
• Naylor, E. et al.: Nat. Chem. Biol., 5, 220 (2009)
• Thai, T.L. et al.: Am. J. Physiol. Renal Physiol., 297, F510 (2009)