(R)-3-(1-(cyclopenta-1,3-dienyl)cycloheptanecarbonyloxy)-1-(2-(5-methylthiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane

ID: ALA3088081

PubChem CID: 72545282

Max Phase: Preclinical

Molecular Formula: C27H38NO2S+

Molecular Weight: 440.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CC[N+]23CCC(CC2)[C@@H](OC(=O)C2(C4=CC=CC4)CCCCCC2)C3)s1

Standard InChI:  InChI=1S/C27H38NO2S/c1-21-10-11-24(31-21)14-19-28-17-12-22(13-18-28)25(20-28)30-26(29)27(23-8-4-5-9-23)15-6-2-3-7-16-27/h4-5,8,10-11,22,25H,2-3,6-7,9,12-20H2,1H3/q+1/t22?,25-,28?/m0/s1

Standard InChI Key:  RBDXMLYCZKSKHX-OKBRVIPFSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   10.2062   -7.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4879   -8.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4790   -8.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2057   -9.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9060   -8.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9166   -8.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6740   -8.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4231   -8.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7796   -7.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4271   -7.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814   -7.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9757   -7.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675   -6.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -6.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9188   -5.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7390   -5.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2868   -5.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1473   -6.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616   -7.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -8.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3576   -9.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0678   -8.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7180   -8.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0969  -10.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7498  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6410  -11.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9206  -11.7656    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0680  -12.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8842  -12.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2384  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4986  -13.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  4  8  1  0
  7  8  1  0
  2  9  1  6
 11 10  1  0
 10 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 10  1  0
 16 17  1  0
 10 18  1  0
 17 18  1  0
 11 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 11  1  0
 12 23  2  0
 12  9  1  0
  4 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  2  0
 28 31  1  0
M  CHG  1   4   1
M  END

Alternative Forms

1. Parent:

   

   ALA3088081

   [(3R)-1-[2-(5-methylthiophen-2-yl)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 1-cyclopenta-1,3-dien-1-ylcycloheptane-1-carboxylate

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: 440.67

Molecular Weight (Monoisotopic): 440.2618

AlogP: 5.98

#Rotatable Bonds: 6

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 0.36

References

1. Mete A, Bowers K, Bull RJ, Coope H, Donald DK, Escott KJ, Ford R, Grime K, Mather A, Ray NC, Russell V..  (2013)  The design of a novel series of muscarinic receptor antagonists leading to AZD8683, a potential inhaled treatment for COPD.,  23  (23): [PMID:24144851] [10.1016/j.bmcl.2013.09.092]

Source

Source(1):

• Scientific Literature