GtoPdb Ligand ID: 7362

Synonyms: compound 10 [PMID: 11495579]
Compound class: Synthetic organic
Comment: JDTic is a potent and selective κ opioid receptor antagonist [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 84.83
Molecular weight 465.3
XLogP 3.76
No. Lipinski's rules broken 0
Canonical SMILES Oc1ccc2c(c1)CNC(C2)C(=O)NC(C(C)C)CN1CCC(C(C1)C)(C)c1cccc(c1)O
Isomeric SMILES Oc1ccc2c(c1)CN[C@H](C2)C(=O)N[C@@H](C(C)C)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O
InChI InChI=1S/C28H39N3O3/c1-18(2)26(30-27(34)25-13-20-8-9-24(33)12-21(20)15-29-25)17-31-11-10-28(4,19(3)16-31)22-6-5-7-23(32)14-22/h5-9,12,14,18-19,25-26,29,32-33H,10-11,13,15-17H2,1-4H3,(H,30,34)/t19-,25+,26+,28+/m0/s1
1. Munro TA, Huang XP, Inglese C, Perrone MG, Van't Veer A, Carroll FI, Béguin C, Carlezon Jr WA, Colabufo NA, Cohen BM et al.. (2013)
Selective κ opioid antagonists nor-BNI, GNTI and JDTic have low affinities for non-opioid receptors and transporters.
PLoS ONE, 8 (8): e70701. [PMID:23976952]
2. Thomas JB, Atkinson RN, Rothman RB, Fix SE, Mascarella SW, Vinson NA, Xu H, Dersch CM, Lu Y, Cantrell BE et al.. (2001)
Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity.
J. Med. Chem., 44 (17): 2687-90. [PMID:11495579]
3. Zaveri NT, Journigan VB, Polgar WE. (2015)
Discovery of the first small-molecule opioid pan antagonist with nanomolar affinity at mu, delta, kappa, and nociceptin opioid receptors.
ACS Chem Neurosci, 6 (4): 646-57. [PMID:25635572]