(1R,3S,5R)-3-(6-chloro-pyridin-3-yloxymethyl)-2-methyl-2-azabicyclo[3.1.0]hexane hydrochloride

ID: ALA4648968

PubChem CID: 156021795

Max Phase: Preclinical

Molecular Formula: C12H16Cl2N2O

Molecular Weight: 238.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1[C@H](COc2ccc(Cl)nc2)C[C@H]2C[C@H]21.Cl

Standard InChI:  InChI=1S/C12H15ClN2O.ClH/c1-15-9(4-8-5-11(8)15)7-16-10-2-3-12(13)14-6-10;/h2-3,6,8-9,11H,4-5,7H2,1H3;1H/t8-,9-,11+;/m0./s1

Standard InChI Key:  WIJZCDGQUPKLRA-WUKJGCQFSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    3.5205   -1.6160    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    1.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186    1.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    0.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    1.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6247    2.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658    1.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0372    1.3500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2165    2.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041    3.4891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4011    2.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    1.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455    0.1372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409    2.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2618    1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632    0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2305    0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    0.1395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 10 11  1  1
  6  5  1  0
 17 14  1  0
  7  9  1  1
 10 15  1  0
  3 12  1  0
  7 10  1  0
  2 16  1  0
  4 13  1  0
  7  8  1  0
  7 15  1  0
  5 13  1  0
 13  2  2  0
  3  6  1  1
  4 14  2  0
  8  3  1  0
 16 17  2  0
  8 18  1  0
 17 19  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 238.72

Molecular Weight (Monoisotopic): 238.0873

AlogP: 2.21

#Rotatable Bonds: 3

Polar Surface Area: 25.36

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.42

CX LogP: 1.86

CX LogD: 0.80

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.76

Np Likeness Score: -0.67

References

1. Nirogi R, Mohammed AR, Shinde AK, Ravella SR, Bogaraju N, Subramanian R, Mekala VR, Palacharla RC, Muddana N, Thentu JB, Bhyrapuneni G, Abraham R, Jasti V..  (2020)  Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression.,  63  (6): [PMID:32026697] [10.1021/acs.jmedchem.9b00790]

Source

Source(1):

• Scientific Literature