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

ID: ALA4093592

PubChem CID: 137654724

Max Phase: Preclinical

Molecular Formula: C13H13Cl2IN4O

Molecular Weight: 439.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(I)n(CC3CCNC3)c2n1

Standard InChI:  InChI=1S/C13H13Cl2IN4O/c14-7-3-8(12(17)21)19-13-9(7)10(15)11(16)20(13)5-6-1-2-18-4-6/h3,6,18H,1-2,4-5H2,(H2,17,21)

Standard InChI Key:  PKHXAHNPTNZSSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   27.6802   -2.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6790   -3.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3938   -4.0524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3920   -2.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1073   -2.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1121   -3.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8996   -3.8858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3815   -3.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8918   -2.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9642   -4.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2501   -3.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9636   -4.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3896   -1.5746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.1591   -4.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2064   -3.2096    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   30.1421   -1.7627    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.6106   -5.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7900   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4588   -5.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0752   -6.5056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7871   -6.0889    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
  8 15  1  0
  9 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093592

   ---

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: 439.08

Molecular Weight (Monoisotopic): 437.9511

AlogP: 2.66

#Rotatable Bonds: 3

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: 11.26

CX LogP: 2.42

CX LogD: -0.83

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: -0.92

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