3-[(2(S)-Azetidinyl)methoxy]-5-[(1S,2R)-2-[2-(N-methylcarbamoyloxy)ethyl]cyclopropyl]pyridine

ID: ALA2024089

PubChem CID: 56951368

Max Phase: Preclinical

Molecular Formula: C16H23N3O3

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)OCC[C@H]1C[C@@H]1c1cncc(OC[C@@H]2CCN2)c1

Standard InChI:  InChI=1S/C16H23N3O3/c1-17-16(20)21-5-3-11-7-15(11)12-6-14(9-18-8-12)22-10-13-2-4-19-13/h6,8-9,11,13,15,19H,2-5,7,10H2,1H3,(H,17,20)/t11-,13-,15-/m0/s1

Standard InChI Key:  HGSHFGWWOPXUPH-WHOFXGATSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.5870   -1.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3522   -1.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2371   -0.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4444   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4433   -2.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1581   -2.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8745   -2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8717   -1.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1563   -1.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299   -1.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0827   -0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859   -0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996   -1.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0135   -1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7295   -1.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4425   -1.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1585   -1.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8714   -1.1650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1616   -2.4052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5874   -1.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  1  0
 12 11  1  1
 12 13  1  0
  2  3  1  0
  6  7  2  0
  1  3  1  0
 13 14  1  0
 14 15  1  0
 15 12  1  0
  1  8  1  1
  7  8  1  0
  2 16  1  6
 16 17  1  0
  8  9  2  0
 17 18  1  0
  9  4  1  0
 18 19  1  0
  4  5  2  0
 19 20  1  0
  4 10  1  0
 19 21  2  0
  1  2  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2024089

   2-[(1R,2S)-2-[5-[[(2S)-azetidin-2-yl]methoxy]pyridin-3-yl]cyclopropyl]ethyl N-methylcarbamate

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: 305.38

Molecular Weight (Monoisotopic): 305.1739

AlogP: 1.67

#Rotatable Bonds: 7

Polar Surface Area: 72.48

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.79

CX LogP: 0.59

CX LogD: -1.74

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: 0.32

References

1. Zhang H, Tückmantel W, Eaton JB, Yuen PW, Yu LF, Bajjuri KM, Fedolak A, Wang D, Ghavami A, Caldarone B, Paterson NE, Lowe DA, Brunner D, Lukas RJ, Kozikowski AP..  (2012)  Chemistry and behavioral studies identify chiral cyclopropanes as selective α4β2-nicotinic acetylcholine receptor partial agonists exhibiting an antidepressant profile.,  55  (2): [PMID:22171543] [10.1021/jm201157c]

2. Zhang HK, Eaton JB, Yu LF, Nys M, Mazzolari A, van Elk R, Smit AB, Alexandrov V, Hanania T, Sabath E, Fedolak A, Brunner D, Lukas RJ, Vistoli G, Ulens C, Kozikowski AP..  (2012)  Insights into the structural determinants required for high-affinity binding of chiral cyclopropane-containing ligands to α4β2-nicotinic acetylcholine receptors: an integrated approach to behaviorally active nicotinic ligands.,  55  (18): [PMID:22928944] [10.1021/jm3008739]

Source

Source(1):

• Scientific Literature