3,4-dichloro-2-phenyl-1-(piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide

ID: ALA4092706

PubChem CID: 137654684

Max Phase: Preclinical

Molecular Formula: C19H18Cl2N4O

Molecular Weight: 389.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(-c3ccccc3)n(C3CCCNC3)c2n1

Standard InChI:  InChI=1S/C19H18Cl2N4O/c20-13-9-14(18(22)26)24-19-15(13)16(21)17(11-5-2-1-3-6-11)25(19)12-7-4-8-23-10-12/h1-3,5-6,9,12,23H,4,7-8,10H2,(H2,22,26)

Standard InChI Key:  LMUQPBXEPPNVJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   41.5804  -21.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5793  -22.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2873  -22.6942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2855  -21.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9941  -21.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9989  -22.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7790  -22.5291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.2563  -21.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7712  -21.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8712  -22.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1639  -22.2841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8706  -23.5104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2831  -20.2396    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.0360  -23.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0192  -20.4260    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   43.4904  -23.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7444  -24.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5442  -24.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0896  -24.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.8352  -23.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0715  -21.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4837  -22.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.3001  -22.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7053  -21.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.2882  -21.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4731  -21.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
  4 13  1  0
  7 14  1  0
  9 15  1  0
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092706

   ---

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: 389.29

Molecular Weight (Monoisotopic): 388.0858

AlogP: 4.03

#Rotatable Bonds: 3

Polar Surface Area: 72.94

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.15

CX LogP: 3.56

CX LogD: 0.93

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -0.62

References

1. Barberis C, Moorcroft N, Pribish J, Tserlin E, Gross A, Czekaj M, Barrague M, Erdman P, Majid T, Batchelor J, Levit M, Hebert A, Shen L, Moreno-Mazza S, Wang A..  (2017)  Discovery of N-substituted 7-azaindoles as Pan-PIM kinase inhibitors - Lead series identification - Part II.,  27  (20): [PMID:28927793] [10.1016/j.bmcl.2017.08.068]

Source

Source(1):

• Scientific Literature