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

ID: ALA4095220

PubChem CID: 137655925

Max Phase: Preclinical

Molecular Formula: C14H15Cl2IN4O

Molecular Weight: 453.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(I)n(C3CCCC(N)C3)c2n1

Standard InChI:  InChI=1S/C14H15Cl2IN4O/c15-8-5-9(13(19)22)20-14-10(8)11(16)12(17)21(14)7-3-1-2-6(18)4-7/h5-7H,1-4,18H2,(H2,19,22)

Standard InChI Key:  MHYXMWPAQOHZQD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   43.9505   -8.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9494   -9.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6638  -10.0817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.6620   -8.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3772   -8.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3819   -9.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1691   -9.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   46.6508   -9.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1612   -8.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2349  -10.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5210   -9.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.2342  -10.9054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.6596   -7.6047    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   46.4285  -10.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4754   -9.2391    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   46.4115   -7.7928    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   45.8779  -11.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1342  -12.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.9413  -12.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4917  -11.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2350  -10.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.2987  -11.8145    0.0000 N   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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095220

   ---

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: 453.11

Molecular Weight (Monoisotopic): 451.9668

AlogP: 3.49

#Rotatable Bonds: 2

Polar Surface Area: 86.93

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.55

CX LogP: 2.93

CX LogD: 0.05

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.68

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