6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-(3-(methylcarbamoyl)pentan-3-yl)picolinamide

ID: ALA3582018

PubChem CID: 71113198

Max Phase: Preclinical

Molecular Formula: C20H28F2N4O3

Molecular Weight: 410.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)(NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1)C(=O)NC

Standard InChI:  InChI=1S/C20H28F2N4O3/c1-4-19(5-2,18(28)23-3)25-16(27)14-8-9-15(26-11-20(21,22)12-26)17(24-14)29-10-13-6-7-13/h8-9,13H,4-7,10-12H2,1-3H3,(H,23,28)(H,25,27)

Standard InChI Key:  JVMZQMRYIYTXKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    5.1972   -1.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1943   -3.0089    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
    3.8924   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -1.6270    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
    2.5973   -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
    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
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    2.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3928    2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906    3.7323    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4291    1.9274    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    1.0841    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
   -2.5972   -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
   -5.3141   -3.7112    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
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -7.2109    0.0000 C   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  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 13  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 22  1  0
 19 25  2  0
 25  9  1  0
  3 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582018

   6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1-ethyl-1-methylcarbamoyl-propyl)-amide

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: 410.47

Molecular Weight (Monoisotopic): 410.2129

AlogP: 2.36

#Rotatable Bonds: 9

Polar Surface Area: 83.56

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.20

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.77

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]

2.  (2016)  Pyridine derivatives as agonists of the CB2 receptor, 

Source

Source(2):

• Scientific Literature
• BindingDB Database