6-(Cyclopropylmethoxy)-N-((1-hydroxycyclohexyl)methyl)-5-(3-methoxyazetidin-1-yl)picolinamide

ID: ALA3582016

PubChem CID: 118418642

Max Phase: Preclinical

Molecular Formula: C21H31N3O4

Molecular Weight: 389.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CN(c2ccc(C(=O)NCC3(O)CCCCC3)nc2OCC2CC2)C1

Standard InChI:  InChI=1S/C21H31N3O4/c1-27-16-11-24(12-16)18-8-7-17(23-20(18)28-13-15-5-6-15)19(25)22-14-21(26)9-3-2-4-10-21/h7-8,15-16,26H,2-6,9-14H2,1H3,(H,22,25)

Standard InChI Key:  LIZJLQKIVJCYJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    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
   -3.6375   -0.9049    0.0000 O   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
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6295   -4.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3292   -5.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -6.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -7.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249   -6.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9293   -5.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 11 10  1  0
  9 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 12  1  0
  2 12  1  0
 16 17  1  0
 14 16  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582016

   6-(cyclopropylmethoxy)-N-[(1-hydroxycyclohexyl)methyl]-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: 389.50

Molecular Weight (Monoisotopic): 389.2315

AlogP: 2.13

#Rotatable Bonds: 8

Polar Surface Area: 83.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.24

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.69

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