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

ID: ALA4089255

PubChem CID: 137644542

Max Phase: Preclinical

Molecular Formula: C13H11Cl2IN4O2

Molecular Weight: 453.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(I)n(C3CCNC(=O)C3)c2n1

Standard InChI:  InChI=1S/C13H11Cl2IN4O2/c14-6-4-7(12(17)22)19-13-9(6)10(15)11(16)20(13)5-1-2-18-8(21)3-5/h4-5H,1-3H2,(H2,17,22)(H,18,21)

Standard InChI Key:  LKXSICYXJDCMQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   42.3422  -14.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3411  -15.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0559  -15.7311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0540  -14.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7694  -14.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7742  -15.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5617  -15.5644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.0436  -14.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5539  -14.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6263  -15.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9122  -15.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6257  -16.5551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0516  -13.2532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.8212  -16.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8685  -14.8882    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   44.8042  -13.4412    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.2703  -16.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5268  -17.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3342  -17.9105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.8848  -17.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6279  -16.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6921  -17.4645    0.0000 O   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
  8 15  1  0
  9 16  1  0
 14 17  1  0
 14 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089255

   ---

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: 453.07

Molecular Weight (Monoisotopic): 451.9304

AlogP: 2.50

#Rotatable Bonds: 2

Polar Surface Area: 90.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.01

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -0.48

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