AC-42   Click here for help

GtoPdb Ligand ID: 289

Synonyms: AC 42 | AC42
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 20.31
Molecular weight 301.24
XLogP 5.46
No. Lipinski's rules broken 1
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Canonical SMILES CCCCC1CCN(CC1)CCCC(=O)c1ccccc1C
Isomeric SMILES CCCCC1CCN(CC1)CCCC(=O)c1ccccc1C
InChI InChI=1S/C20H31NO/c1-3-4-9-18-12-15-21(16-13-18)14-7-11-20(22)19-10-6-5-8-17(19)2/h5-6,8,10,18H,3-4,7,9,11-16H2,1-2H3
1. Avlani VA, Langmead CJ, Guida E, Wood MD, Tehan BG, Herdon HJ, Watson JM, Sexton PM, Christopoulos A. (2010)
Orthosteric and allosteric modes of interaction of novel selective agonists of the M1 muscarinic acetylcholine receptor.
Mol Pharmacol, 78 (1): 94-104. [PMID:20413650]
2. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
3. Jones CK, Brady AE, Davis AA, Xiang Z, Bubser M, Tantawy MN, Kane AS, Bridges TM, Kennedy JP, Bradley SR et al.. (2008)
Novel selective allosteric activator of the M1 muscarinic acetylcholine receptor regulates amyloid processing and produces antipsychotic-like activity in rats.
J Neurosci, 28 (41): 10422-33. [PMID:18842902]
4. Keov P, Valant C, Devine SM, Lane JR, Scammells PJ, Sexton PM, Christopoulos A. (2013)
Reverse engineering of the selective agonist TBPB unveils both orthosteric and allosteric modes of action at the M₁ muscarinic acetylcholine receptor.
Mol Pharmacol, 84 (3): 425-37. [PMID:23798605]
5. Langmead CJ, Austin NE, Branch CL, Brown JT, Buchanan KA, Davies CH, Forbes IT, Fry VA, Hagan JJ, Herdon HJ et al.. (2008)
Characterization of a CNS penetrant, selective M1 muscarinic receptor agonist, 77-LH-28-1.
Br J Pharmacol, 154 (5): 1104-15. [PMID:18454168]
6. Langmead CJ, Fry VA, Forbes IT, Branch CL, Christopoulos A, Wood MD, Herdon HJ. (2006)
Probing the molecular mechanism of interaction between 4-n-butyl-1-[4-(2-methylphenyl)-4-oxo-1-butyl]-piperidine (AC-42) and the muscarinic M(1) receptor: direct pharmacological evidence that AC-42 is an allosteric agonist.
Mol Pharmacol, 69 (1): 236-46. [PMID:16207821]
7. May LT, Avlani VA, Langmead CJ, Herdon HJ, Wood MD, Sexton PM, Christopoulos A. (2007)
Structure-function studies of allosteric agonism at M2 muscarinic acetylcholine receptors.
Mol Pharmacol, 72 (2): 463-76. [PMID:17525129]
8. Richards MH, van Giersbergen PL. (1995)
Human muscarinic receptors expressed in A9L and CHO cells: activation by full and partial agonists.
Br J Pharmacol, 114 (6): 1241-9. [PMID:7620715]
9. Sams AG, Hentzer M, Mikkelsen GK, Larsen K, Bundgaard C, Plath N, Christoffersen CT, Bang-Andersen B. (2010)
Discovery of N-{1-[3-(3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): an allosteric muscarinic M1 receptor agonist with unprecedented selectivity and procognitive potential.
J Med Chem, 53 (17): 6386-97. [PMID:20684563]
10. Spalding TA, Ma JN, Ott TR, Friberg M, Bajpai A, Bradley SR, Davis RE, Brann MR, Burstein ES. (2006)
Structural requirements of transmembrane domain 3 for activation by the M1 muscarinic receptor agonists AC-42, AC-260584, clozapine, and N-desmethylclozapine: evidence for three distinct modes of receptor activation.
Mol Pharmacol, 70 (6): 1974-83. [PMID:16959945]
11. Spalding TA, Trotter C, Skjaerbaek N, Messier TL, Currier EA, Burstein ES, Li D, Hacksell U, Brann MR. (2002)
Discovery of an ectopic activation site on the M(1) muscarinic receptor.
Mol Pharmacol, 61 (6): 1297-302. [PMID:12021390]
12. Sur C, Mallorga PJ, Wittmann M, Jacobson MA, Pascarella D, Williams JB, Brandish PE, Pettibone DJ, Scolnick EM, Conn PJ. (2003)
N-desmethylclozapine, an allosteric agonist at muscarinic 1 receptor, potentiates N-methyl-D-aspartate receptor activity.
Proc Natl Acad Sci USA, 100 (23): 13674-9. [PMID:14595031]