3-{[(1R)-2-[(2R)-2-{[(adamantan-2-yloxy)carbonyl]amino}-3-(1H-indol-3-yl)-2-methylpropanamido]-1-phenylethyl]carbamoyl}propanoic acid

• ChemBase ID: 164745
• Molecular Formular: C35H42N4O6
• Molecular Mass: 614.73118
• Monoisotopic Mass: 614.31043508
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@@](NC(=O)OC1C2CC3CC(C2)CC1C3)(C(=O)NC[C@H](NC(=O)CCC(=O)O)c1ccccc1)C
• Canonical SMILES: O=C(N[C@H](c1ccccc1)CNC(=O)[C@@](Cc1c[nH]c2c1cccc2)(NC(=O)OC1C2CC3CC1CC(C2)C3)C)CCC(=O)O
• InChI: InChI=1S/C35H42N4O6/c1-35(18-26-19-36-28-10-6-5-9-27(26)28,39-34(44)45-32-24-14-21-13-22(16-24)17-25(32)15-21)33(43)37-20-29(23-7-3-2-4-8-23)38-30(40)11-12-31(41)42/h2-10,19,21-22,24-25,29,32,36H,11-18,20H2,1H3,(H,37,43)(H,38,40)(H,39,44)(H,41,42)/t21?,22?,24?,25?,29-,32?,35+/m0/s1
• InChIKey: FVQSSYMRZKLFDR-ZABPBAJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1R)-2-[(2R)-2-{[(adamantan-2-yloxy)carbonyl]amino}-3-(1H-indol-3-yl)-2-methylpropanamido]-1-phenylethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1R)-2-[(2R)-2-{[(adamantan-2-yloxy)carbonyl]amino}-3-(1H-indol-3-yl)-2-methylpropanamido]-1-phenylethyl]carbamoyl}propanoic acid
• Synonyms: 4-[[(1R)-2-[[(2R)-3-(1H-Indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]amino]propyl]amino]-1-phenylethyl]amino]-4-oxobutanoic Acid; CI 988; [R-(R*,R*)]-4-[[2-[[3-(1H-Indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]amino]propyl]amino]-1-phenylethyl]amino]-4-oxobutanoic Acid; CI-988

Database IDs

• CAS Number: 130332-27-3
• PubChem SID: 162258880
• PubChem CID: 108187

CALCULATED PROPERTIES

• Acid pKa: 4.179471
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 2.932648
• LogD (pH = 7.4): 1.223462
• Log P: 4.2707825
• Molar Refractivity: 166.7223 cm^3
• Polarizability: 66.4408 Å^3
• Polar Surface Area: 149.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C432695

CI-988 is a potent and selective cholecystokinin 2 (CCK-2) receptor antagonist that displays ~ 1600-fold selectivity over CCK1 receptors and has negligible affinity at other binding sites. CI-988 exhibits anxiolytic activity following oral administration.

REFERENCES

• Drysdale, M. et al.: Bioorg. Med. Chem. Lett., 2, 45 (1992)
• Moody, T.W. et al.: J. Pharmacol. Exp. Ther., 299, 1154 (1992)