ID: ALA471980

Max Phase: Preclinical

Molecular Formula: C26H35N3O2

Molecular Weight: 421.59

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCOc1ccc(Cc2nc3cc(C(=O)N(CC)CC)ccc3n2CCC(C)C)cc1

Standard InChI:  InChI=1S/C26H35N3O2/c1-6-28(7-2)26(30)21-11-14-24-23(18-21)27-25(29(24)16-15-19(4)5)17-20-9-12-22(13-10-20)31-8-3/h9-14,18-19H,6-8,15-17H2,1-5H3

Standard InChI Key:  RLLSCGRLMPJHDQ-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 421.59

Molecular Weight (Monoisotopic): 421.2729

AlogP: 5.55

#Rotatable Bonds: 10

Polar Surface Area: 47.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 4.66

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.67

References

1. Pagé D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, Wei Z, Woo S, Luo X, Cheng YX, Yang H, Srivastava S, Zhou F, Brown W, Tomaszewski M, Walpole C, Hodzic L, St-Onge S, Godbout C, Salois D, Payza K..  (2008)  Novel benzimidazole derivatives as selective CB2 agonists.,  18  (13): [PMID:18522867] [10.1016/j.bmcl.2008.05.073]

2. Nimczick M, Pemp D, Darras FH, Chen X, Heilmann J, Decker M..  (2014)  Synthesis and biological evaluation of bivalent cannabinoid receptor ligands based on hCB₂R selective benzimidazoles reveal unexpected intrinsic properties.,  22  (15): [PMID:24984935] [10.1016/j.bmc.2014.06.008]

3. Dolles D, Hoffmann M, Gunesch S, Marinelli O, Möller J, Santoni G, Chatonnet A, Lohse MJ, Wittmann HJ, Strasser A, Nabissi M, Maurice T, Decker M..  (2018)  Structure-Activity Relationships and Computational Investigations into the Development of Potent and Balanced Dual-Acting Butyrylcholinesterase Inhibitors and Human Cannabinoid Receptor 2 Ligands with Pro-Cognitive in Vivo Profiles.,  61  (4): [PMID:29400965] [10.1021/acs.jmedchem.7b01760]

4. Scheiner M, Dolles D, Gunesch S, Hoffmann M, Nabissi M, Marinelli O, Naldi M, Bartolini M, Petralla S, Poeta E, Monti B, Falkeis C, Vieth M, Hübner H, Gmeiner P, Maitra R, Maurice T, Decker M..  (2019)  Dual-Acting Cholinesterase-Human Cannabinoid Receptor 2 Ligands Show Pronounced Neuroprotection in Vitro and Overadditive and Disease-Modifying Neuroprotective Effects in Vivo.,  62  (20): [PMID:31609608] [10.1021/acs.jmedchem.9b00623]

5. Mangiatordi GF, Intranuovo F, Delre P, Abatematteo FS, Abate C, Niso M, Creanza TM, Ancona N, Stefanachi A, Contino M..  (2020)  Cannabinoid Receptor Subtype 2 (CB2R) in a Multitarget Approach: Perspective of an Innovative Strategy in Cancer and Neurodegeneration.,  63  (23.0): [PMID:33094613] [10.1021/acs.jmedchem.0c01357]

Source

Source(1):

• Scientific Literature