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

ID: ALA4100435

PubChem CID: 137659327

Max Phase: Preclinical

Molecular Formula: C18H18Cl2N4O

Molecular Weight: 377.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(C#CC3CC3)n(C3CCCNC3)c2n1

Standard InChI:  InChI=1S/C18H18Cl2N4O/c19-12-8-13(17(21)25)23-18-15(12)16(20)14(6-5-10-3-4-10)24(18)11-2-1-7-22-9-11/h8,10-11,22H,1-4,7,9H2,(H2,21,25)

Standard InChI Key:  MPFTYTXJRHGYBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   12.7233  -27.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7222  -28.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4370  -28.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4352  -27.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1506  -27.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1555  -28.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9429  -28.6023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4249  -27.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9350  -27.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0075  -28.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2933  -28.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0068  -29.5930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4327  -26.2910    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.2024  -29.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1854  -26.4790    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.6516  -29.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9080  -30.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7154  -30.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2660  -30.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0092  -29.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2498  -27.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0748  -27.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8997  -27.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6141  -28.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6092  -27.4932    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  3  0
  8 21  1  0
 22 23  1  0
 24 23  1  0
 25 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100435

   ---

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: 377.28

Molecular Weight (Monoisotopic): 376.0858

AlogP: 3.13

#Rotatable Bonds: 2

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: 9.96

CX LogP: 3.17

CX LogD: 0.68

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.46

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