N-(3-(2-Amino-2-oxoethyl)oxetan-3-yl)-6-(cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)picolinamide

ID: ALA3582013

PubChem CID: 118418664

Max Phase: Preclinical

Molecular Formula: C19H26N4O5

Molecular Weight: 390.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CN(c2ccc(C(=O)NC3(CC(N)=O)COC3)nc2OCC2CC2)C1

Standard InChI:  InChI=1S/C19H26N4O5/c1-26-13-7-23(8-13)15-5-4-14(21-18(15)28-9-12-2-3-12)17(25)22-19(6-16(20)24)10-27-11-19/h4-5,12-13H,2-3,6-11H2,1H3,(H2,20,24)(H,22,25)

Standard InChI Key:  DVRPSQSROOCQMI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2604   -4.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033   -2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -3.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0035    1.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3894    2.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399    2.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    3.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775    4.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -5.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901   -6.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -5.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5880   -7.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 13 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 16  1  0
  6 16  1  0
 20 21  1  0
 18 20  1  0
  9 22  1  0
 22 23  1  0
 22 24  2  0
 23  1  1  0
  1 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582013

   N-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-(cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)pyridine-2-carboxamide

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: 390.44

Molecular Weight (Monoisotopic): 390.1903

AlogP: 0.08

#Rotatable Bonds: 9

Polar Surface Area: 116.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.22

CX LogP: 0.06

CX LogD: 0.06

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.72

References

1. Slavik R, Grether U, Müller Herde A, Gobbi L, Fingerle J, Ullmer C, Krämer SD, Schibli R, Mu L, Ametamey SM..  (2015)  Discovery of a high affinity and selective pyridine analog as a potential positron emission tomography imaging agent for cannabinoid type 2 receptor.,  58  (10): [PMID:25950914] [10.1021/acs.jmedchem.5b00283]

Source

Source(1):

• Scientific Literature