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

ID: ALA4071926

PubChem CID: 137638981

Max Phase: Preclinical

Molecular Formula: C17H20Cl2N4O

Molecular Weight: 367.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=Cc1c(Cl)c2c(Cl)cc(C(N)=O)nc2n1C1CCCNC1

Standard InChI:  InChI=1S/C17H20Cl2N4O/c1-9(2)6-13-15(19)14-11(18)7-12(16(20)24)22-17(14)23(13)10-4-3-5-21-8-10/h6-7,10,21H,3-5,8H2,1-2H3,(H2,20,24)

Standard InChI Key:  WVOATLASLUXFNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.6471  -27.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459  -27.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3540  -28.3402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522  -26.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608  -27.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656  -27.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456  -28.1752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3230  -27.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8379  -26.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379  -28.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305  -27.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372  -29.1565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3497  -25.8857    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1026  -28.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858  -26.0720    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5570  -29.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8111  -30.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6108  -30.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1562  -29.8893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9018  -29.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1401  -27.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446  -26.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3617  -26.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1318  -26.0899    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
  8 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071926

   ---

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: 367.28

Molecular Weight (Monoisotopic): 366.1014

AlogP: 3.79

#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: 10.00

CX LogP: 3.28

CX LogD: 0.77

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: -0.42

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