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

ID: ALA4086532

PubChem CID: 137642902

Max Phase: Preclinical

Molecular Formula: C14H14Cl2IN3O2

Molecular Weight: 454.10

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H14Cl2IN3O2/c15-8-5-9(13(18)22)19-14-10(8)11(16)12(17)20(14)6-2-1-3-7(21)4-6/h5-7,21H,1-4H2,(H2,18,22)

Standard InChI Key:  BXKIPOGUQCAVMR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   35.0326  -14.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0315  -15.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7459  -16.2162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7441  -14.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4592  -14.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4641  -15.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2512  -16.0496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7328  -15.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2433  -14.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3170  -16.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6032  -15.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3163  -17.0398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7417  -13.7392    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.5105  -16.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5574  -15.3736    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   37.4936  -13.9273    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.9599  -17.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2163  -18.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0233  -18.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5737  -17.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3170  -16.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3807  -17.9489    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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086532

   ---

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: 454.10

Molecular Weight (Monoisotopic): 452.9508

AlogP: 3.52

#Rotatable Bonds: 2

Polar Surface Area: 81.14

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.98

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.04

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -0.21

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