MQ1   Click here for help

GtoPdb Ligand ID: 8587

Synonyms: compound (R)-10a [1] | MQ-1
Compound class: Synthetic organic
Comment: MQ1 is reported as a negative allosteric modulator (NAM) of the melanin-concentrating hormone receptor 1 (MCHR1) [1-2]. Antagonists and NAMs of MCHR1 are being investigated for their potential to provide anti-obesity therapies.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 54.46
Molecular weight 429.24
XLogP 4.76
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1ccc(cc1)OCC1CC1)Nc1ccc2c(c1C)ncc(c2)C(N1CCCC1)C
Isomeric SMILES O=C(c1ccc(cc1)OCC1CC1)Nc1ccc2c(c1C)ncc(c2)[C@H](N1CCCC1)C
InChI InChI=1S/C27H31N3O2/c1-18-25(29-27(31)21-7-10-24(11-8-21)32-17-20-5-6-20)12-9-22-15-23(16-28-26(18)22)19(2)30-13-3-4-14-30/h7-12,15-16,19-20H,3-6,13-14,17H2,1-2H3,(H,29,31)/t19-/m1/s1
1. Kasai S, Kamata M, Masada S, Kunitomo J, Kamaura M, Okawa T, Takami K, Ogino H, Nakano Y, Ashina S et al.. (2012)
Synthesis, structure-activity relationship, and pharmacological studies of novel melanin-concentrating hormone receptor 1 antagonists 3-aminomethylquinolines: reducing human ether-a-go-go-related gene (hERG) associated liabilities.
J Med Chem, 55 (9): 4336-51. [PMID:22490048]
2. Sakurai T, Ogawa K, Ishihara Y, Kasai S, Nakayama M. (2014)
The MCH(1) receptor, an anti-obesity target, is allosterically inhibited by 8-methylquinoline derivatives possessing subnanomolar binding and long residence times.
Br J Pharmacol, 171 (5): 1287-98. [PMID:24670150]