6-(Cyclopropylmethoxy)-N-(3-(1-hydroxy-2-methylpropan-2-yl)isoxazol-5-yl)-5-(3-methoxyazetidin-1-yl)picolinamide

ID: ALA3582014

PubChem CID: 122179273

Max Phase: Preclinical

Molecular Formula: C20H26N4O5

Molecular Weight: 402.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CN(c2ccc(C(=O)OC(C)(C)c3cc(N)on3)nc2OCC2CC2)C1

Standard InChI:  InChI=1S/C20H26N4O5/c1-20(2,16-8-17(21)29-23-16)28-19(25)14-6-7-15(24-9-13(10-24)26-3)18(22-14)27-11-12-4-5-12/h6-8,12-13H,4-5,9-11,21H2,1-3H3

Standard InChI Key:  JZTWQTQJHAUDDA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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 O   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
   -5.1035   -6.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6379   -7.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379   -7.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6764   -6.1158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -8.5171    0.0000 N   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
   -4.9336   -3.1588    0.0000 C   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
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
 24 27  1  0
 21 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582014

   ---

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: 402.45

Molecular Weight (Monoisotopic): 402.1903

AlogP: 2.37

#Rotatable Bonds: 8

Polar Surface Area: 112.94

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.40

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.66

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