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

ID: ALA4096630

PubChem CID: 137654577

Max Phase: Preclinical

Molecular Formula: C17H20Cl2N4O2

Molecular Weight: 383.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC/C=C/c1c(Cl)c2c(Cl)cc(C(N)=O)nc2n1C1CCCNC1

Standard InChI:  InChI=1S/C17H20Cl2N4O2/c1-25-7-3-5-13-15(19)14-11(18)8-12(16(20)24)22-17(14)23(13)10-4-2-6-21-9-10/h3,5,8,10,21H,2,4,6-7,9H2,1H3,(H2,20,24)/b5-3+

Standard InChI Key:  HMSVYVJNUGHJAR-HWKANZROSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   25.4347   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4335   -3.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1416   -4.4064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1398   -2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8484   -3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8532   -3.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6333   -4.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1106   -3.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6255   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7255   -4.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0181   -3.9963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7249   -5.2227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1374   -1.9519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.8903   -5.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8735   -2.1382    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.3446   -5.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5987   -6.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3985   -6.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9439   -5.9555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6894   -5.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9278   -3.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3322   -2.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494   -2.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5538   -2.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3710   -2.1416    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
  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
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096630

   ---

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: 3.03

#Rotatable Bonds: 5

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: 10.00

CX LogP: 2.40

CX LogD: -0.11

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.25

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