ICI-199441   Click here for help

GtoPdb Ligand ID: 11691

Synonyms: ICI 199,441 | ICI199441 | ligand 1 [PMID: 8893842]
Compound class: Synthetic organic
Comment: ICI-199441 is a κ opioid receptor agonist [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 23.55
Molecular weight 390.13
XLogP 4.8
No. Lipinski's rules broken 0
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Canonical SMILES O=C(N([C@@H](c1ccccc1)CN1CCCC1)C)Cc1ccc(c(c1)Cl)Cl
Isomeric SMILES Clc1cc(ccc1Cl)CC(=O)N([C@H](CN1CCCC1)c1ccccc1)C
InChI InChI=1S/C21H24Cl2N2O/c1-24(21(26)14-16-9-10-18(22)19(23)13-16)20(15-25-11-5-6-12-25)17-7-3-2-4-8-17/h2-4,7-10,13,20H,5-6,11-12,14-15H2,1H3/t20-/m1/s1
1. Chang AC, Cowan A, Takemori AE, Portoghese PS. (1996)
Aspartic acid conjugates of 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1(3-aminophenyl)-2-(1-pyrrolidi nyl) ethyl]acetamide: kappa opioid receptor agonists with limited access to the central nervous system.
J Med Chem, 39 (22): 4478-82. [PMID:8893842]
2. Kumar V, Guo D, Daubert JD, Cassel JA, DeHaven RN, Mansson E, DeHaven-Hudkins DL, Maycock AL. (2005)
Amino acid conjugates as kappa opioid receptor agonists.
Bioorg Med Chem Lett, 15 (5): 1279-82. [PMID:15713370]
3. Kumar V, Guo D, Marella M, Cassel JA, Dehaven RN, Daubert JD, Mansson E. (2008)
Use of receptor chimeras to identify small molecules with high affinity for the dynorphin A binding domain of the kappa opioid receptor.
Bioorg Med Chem Lett, 18 (12): 3667-71. [PMID:18487043]