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

ID: ALA4087517

PubChem CID: 137644367

Max Phase: Preclinical

Molecular Formula: C15H17Cl2IN4O

Molecular Weight: 467.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCC1CCC(n2c(I)c(Cl)c3c(Cl)cc(C(N)=O)nc32)CC1

Standard InChI:  InChI=1S/C15H17Cl2IN4O/c16-9-5-10(14(20)23)21-15-11(9)12(17)13(18)22(15)8-3-1-7(6-19)2-4-8/h5,7-8H,1-4,6,19H2,(H2,20,23)

Standard InChI Key:  USAPQYPKDFTEMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   11.1692  -15.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1680  -16.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8828  -16.4816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8810  -14.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5964  -15.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6012  -16.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3886  -16.3149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8706  -15.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3809  -14.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4532  -16.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7391  -16.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4526  -17.3055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8786  -14.0036    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6482  -17.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6956  -15.6386    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   13.6311  -14.1916    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0973  -17.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3538  -18.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1612  -18.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7117  -18.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4549  -17.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4178  -19.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8670  -20.0593    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
 19 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087517

   ---

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: 467.14

Molecular Weight (Monoisotopic): 465.9824

AlogP: 3.74

#Rotatable Bonds: 3

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: 10.22

CX LogP: 3.31

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.80

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