6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-(2-(5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl)propan-2-yl)picolinamide

ID: ALA3582020

PubChem CID: 122179276

Max Phase: Preclinical

Molecular Formula: C23H24F2N6O3

Molecular Weight: 470.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1)c1nnc(-c2cccnc2)o1

Standard InChI:  InChI=1S/C23H24F2N6O3/c1-22(2,21-30-29-19(34-21)15-4-3-9-26-10-15)28-18(32)16-7-8-17(31-12-23(24,25)13-31)20(27-16)33-11-14-5-6-14/h3-4,7-10,14H,5-6,11-13H2,1-2H3,(H,28,32)

Standard InChI Key:  FENJHNQEXSOWIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  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
   -4.9336   -3.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956   -2.5570    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
   -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
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4276    1.9362    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837    3.7381    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1035   -6.1193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6379   -7.5452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379   -7.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6764   -6.1158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540   -8.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565  -10.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843  -11.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3090  -11.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1943   -9.6226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778   -8.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
 14 13  1  0
 12 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 15  1  0
  5 15  1  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
 20  1  1  0
  1 22  1  0
 17 23  1  0
 17 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 22  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582020

   ---

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: 470.48

Molecular Weight (Monoisotopic): 470.1878

AlogP: 3.44

#Rotatable Bonds: 8

Polar Surface Area: 106.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.57

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.53

Np Likeness Score: -1.24

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