2-(2-{4-[4-(diethylamino)butyl]piperidin-1-yl}acetyl)-2,9-diazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

ID: ALA295388

Chembl Id: CHEMBL295388

Cas Number: 142860-99-9

PubChem CID: 372625

Max Phase: Preclinical

Molecular Formula: C28H38N4O2

Molecular Weight: 462.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCCC1CCN(CC(=O)N2c3ccccc3NC(=O)c3ccccc32)CC1

Standard InChI:  InChI=1S/C28H38N4O2/c1-3-30(4-2)18-10-9-11-22-16-19-31(20-17-22)21-27(33)32-25-14-7-5-12-23(25)28(34)29-24-13-6-8-15-26(24)32/h5-8,12-15,22H,3-4,9-11,16-21H2,1-2H3,(H,29,34)

Standard InChI Key:  SRLMLQNXERJQPS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA295388

   5-((4-(4-(Diethylamino)butyl)-1-piperidinyl)acetyl)-10,11-dihydrobenzo(b,e)(1,4)diazepine-11-one

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

Calculated Properties

Molecular Weight: 462.64

Molecular Weight (Monoisotopic): 462.2995

AlogP: 5.14

#Rotatable Bonds: 9

Polar Surface Area: 55.89

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.33

CX LogP: 4.20

CX LogD: 1.16

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.52

Np Likeness Score: -0.77

References

1. Cohen VI, Baumgold J, Jin B, De La Cruz R, Rzeszotarski WJ, Reba RC..  (1993)  Synthesis and structure-activity relationship of some 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]-10,11-dihydro-5H- benzo[b,e][1,4]diazepin-11-ones as M2-selective antimuscarinics.,  36  (1): [PMID:8421282] [10.1021/jm00053a021]

2. PubChem BioAssay data set, 

3. Pegoli A, Wifling D, Gruber CG, She X, Hübner H, Bernhardt G, Gmeiner P, Keller M..  (2019)  Conjugation of Short Peptides to Dibenzodiazepinone-Type Muscarinic Acetylcholine Receptor Ligands Determines M₂R Selectivity.,  62  (11): [PMID:31074983] [10.1021/acs.jmedchem.8b01967]

4. Gruber, Corinna G., Pegoli, Andrea, Muller, Christoph, Gratz, Lukas, She, Xueke, Keller, Max.  (2020)  Differently fluorescence-labelled dibenzodiazepinone-type muscarinic acetylcholine receptor ligands with high M2R affinity,  11  (7.0): [PMID:33479678] [10.1039/d0md00137f]

5. Weinhart CG, Wifling D, Schmidt MF, Neu E, Höring C, Clark T, Gmeiner P, Keller M..  (2021)  Dibenzodiazepinone-type muscarinic receptor antagonists conjugated to basic peptides: Impact of the linker moiety and unnatural amino acids on M₂R selectivity.,  213  [PMID:33571911] [10.1016/j.ejmech.2021.113159]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays