3,4-dichloro-1-(piperidin-3-yl)-2-(tetrahydrofuran-2-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide

ID: ALA4073332

PubChem CID: 137640893

Max Phase: Preclinical

Molecular Formula: C17H20Cl2N4O2

Molecular Weight: 383.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(C3CCCO3)n(C3CCCNC3)c2n1

Standard InChI:  InChI=1S/C17H20Cl2N4O2/c18-10-7-11(16(20)24)22-17-13(10)14(19)15(12-4-2-6-25-12)23(17)9-3-1-5-21-8-9/h7,9,12,21H,1-6,8H2,(H2,20,24)

Standard InChI Key:  NPHICJWCOYEVRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.0238   -3.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -3.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -4.2496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290   -2.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376   -3.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4424   -3.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -4.0846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998   -3.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2146   -2.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147   -4.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -3.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3140   -5.0659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.7950    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4794   -4.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4626   -1.9814    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9338   -5.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9876   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330   -5.7987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2786   -5.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5144   -3.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987   -4.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7744   -3.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696   -3.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9909   -2.7524    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
  9 15  1  0
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4073332

   ---

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: 383.28

Molecular Weight (Monoisotopic): 382.0963

AlogP: 3.22

#Rotatable Bonds: 3

Polar Surface Area: 82.17

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.99

CX LogP: 2.25

CX LogD: -0.25

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: -0.57

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