2-((2S,4R)-4-(8-chloro-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)tetrahydro-2H-pyran-2-yl)acetonitrile

ID: ALA4549553

PubChem CID: 142423880

Max Phase: Preclinical

Molecular Formula: C19H19ClN4O

Molecular Weight: 354.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1nc2cnc3ccc(Cl)cc3c2n1[C@@H]1CCO[C@H](CC#N)C1

Standard InChI:  InChI=1S/C19H19ClN4O/c1-2-18-23-17-11-22-16-4-3-12(20)9-15(16)19(17)24(18)13-6-8-25-14(10-13)5-7-21/h3-4,9,11,13-14H,2,5-6,8,10H2,1H3/t13-,14-/m1/s1

Standard InChI Key:  JJHOHPOGCOEIHB-ZIAGYGMSSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.9313   -3.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -4.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366   -4.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3419   -4.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3419   -3.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366   -2.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0490   -4.4649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650   -5.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639   -6.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719   -6.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701   -5.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -5.2665    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1788   -5.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1795   -6.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881   -6.8974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5963   -6.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8825   -5.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5883   -5.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -5.1191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577   -4.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2639   -3.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811   -3.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6366   -2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -1.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0520   -1.1909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  6
  8  9  2  0
  9 10  1  0
 10 14  2  0
 13 11  2  0
 11  8  1  0
  8 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 18  1  0
 17 13  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  7  1  0
  7 17  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  6
 23 24  1  0
 24 25  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549553

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.84

Molecular Weight (Monoisotopic): 354.1247

AlogP: 4.43

#Rotatable Bonds: 3

Polar Surface Area: 63.73

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.95

CX LogP: 2.86

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.96

References

1. Rosse G..  (2019)  Imidazoquinolines as Novel Inhibitors of LRRK2 Kinase Activity.,  10  (2): [PMID:30783493] [10.1021/acsmedchemlett.8b00654]

Source

Source(1):

• Scientific Literature