N-(2-Cyano-2-methylpropyl)-2-(1-((1r,4r)-4-(cyanomethyl)cyclohexyl)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)acetamide

ID: ALA4537718

PubChem CID: 134611580

Max Phase: Preclinical

Molecular Formula: C23H27N7O

Molecular Weight: 417.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C#N)CNC(=O)Cc1nc2cnc3[nH]ccc3c2n1[C@H]1CC[C@H](CC#N)CC1

Standard InChI:  InChI=1S/C23H27N7O/c1-23(2,13-25)14-28-20(31)11-19-29-18-12-27-22-17(8-10-26-22)21(18)30(19)16-5-3-15(4-6-16)7-9-24/h8,10,12,15-16H,3-7,11,14H2,1-2H3,(H,26,27)(H,28,31)/t15-,16-

Standard InChI Key:  CRBPNYKHFXDNRW-WKILWMFISA-N

Molfile:  

 
     RDKit          2D

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    7.6268  -26.8049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3337  -25.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1169  -26.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6006  -25.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1165  -25.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9199  -25.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233  -25.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4532  -24.3742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6447  -24.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3152  -25.0334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9991  -23.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8018  -23.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3469  -23.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0972  -22.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2971  -22.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7467  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6454  -21.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4444  -22.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2451  -22.2979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2350  -23.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4178  -23.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0103  -24.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082  -22.8773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910  -22.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814  -22.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9642  -22.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1889  -21.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678  -21.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543  -20.7435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0
  1  2  1  0
  2  4  2  0
  3  9  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 10  1  1
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  6
 19 20  1  0
 20 21  3  0
 11 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537718

   ---

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: 417.52

Molecular Weight (Monoisotopic): 417.2277

AlogP: 3.77

#Rotatable Bonds: 6

Polar Surface Area: 123.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.90

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -0.85

References

1. Leonard KA, Madge LA, Krawczuk PJ, Wang A, Kreutter KD, Bacani GM, Chai W, Smith RC, Tichenor MS, Harris MC, Malaviya R, Seierstad M, Johnson ME, Venable JD, Kim S, Hirst GC, Mathur AS, Rao TS, Edwards JP, Rizzolio MC, Koudriakova T..  (2020)  Discovery of a Gut-Restricted JAK Inhibitor for the Treatment of Inflammatory Bowel Disease.,  63  (6): [PMID:32134643] [10.1021/acs.jmedchem.9b01439]

Source

Source(1):

• Scientific Literature