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

ID: ALA4090269

PubChem CID: 137643747

Max Phase: Preclinical

Molecular Formula: C18H22Cl2N4O2

Molecular Weight: 397.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCC1CC1c1c(Cl)c2c(Cl)cc(C(N)=O)nc2n1C1CCCNC1

Standard InChI:  InChI=1S/C18H22Cl2N4O2/c1-26-8-9-5-11(9)16-15(20)14-12(19)6-13(17(21)25)23-18(14)24(16)10-3-2-4-22-7-10/h6,9-11,22H,2-5,7-8H2,1H3,(H2,21,25)

Standard InChI Key:  VNPQQGXWMYSECL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   38.0599  -27.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0587  -28.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7668  -28.5301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7650  -26.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4736  -27.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4784  -28.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2584  -28.3650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7358  -27.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2507  -27.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3507  -28.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6433  -28.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3501  -29.3463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7626  -26.0755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.5155  -29.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4987  -26.2619    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.9698  -29.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2239  -30.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0237  -30.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5690  -30.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3146  -29.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5537  -27.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2638  -28.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2590  -27.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6766  -28.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4937  -28.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.9065  -29.5039    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
 22 21  1  0
 23 22  1  0
 21 23  1  0
  8 21  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090269

   ---

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: 397.31

Molecular Weight (Monoisotopic): 396.1120

AlogP: 3.12

#Rotatable Bonds: 5

Polar Surface Area: 82.17

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.01

CX LogP: 2.19

CX LogD: -0.33

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: -0.18

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