Ethyl 2-(6-(Cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)picolinamido)-2-ethylbutanoate

ID: ALA3582008

PubChem CID: 118418701

Max Phase: Preclinical

Molecular Formula: C22H33N3O5

Molecular Weight: 419.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H33N3O5/c1-5-22(6-2,21(27)29-7-3)24-19(26)17-10-11-18(25-12-16(13-25)28-4)20(23-17)30-14-15-8-9-15/h10-11,15-16H,5-9,12-14H2,1-4H3,(H,24,26)

Standard InChI Key:  IXMCJACYFJDRFX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.1943   -3.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2329   -3.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7579   -1.7260    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
    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
    3.8990   -0.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1972   -1.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -1.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -2.7654    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
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 O   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
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2252   -8.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
  4  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 16 15  1  0
 14 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 17  1  0
  7 17  1  0
 21 22  1  0
 19 21  1  0
 10 23  1  0
 23 24  1  0
 23 25  2  0
 24  1  1  0
  1 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3582008

   Ethyl 2-(6-(cyclopropylmethoxy)-5-(3-methoxyazetidin-1-yl)picolinamido)-2-ethylbutanoate

2. Alternative Forms:

   

   ALA3582008

   ---

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: 419.52

Molecular Weight (Monoisotopic): 419.2420

AlogP: 2.56

#Rotatable Bonds: 11

Polar Surface Area: 89.99

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.21

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.75

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