(S)-2-(5-amino-4,4-dimethyl-5-oxopent-1-ynyl)-3,4-dichloro-1-(piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide

ID: ALA4533366

PubChem CID: 155547453

Max Phase: Preclinical

Molecular Formula: C20H23Cl2N5O2

Molecular Weight: 436.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(CC#Cc1c(Cl)c2c(Cl)cc(C(N)=O)nc2n1[C@H]1CCCNC1)C(N)=O

Standard InChI:  InChI=1S/C20H23Cl2N5O2/c1-20(2,19(24)29)7-3-6-14-16(22)15-12(21)9-13(17(23)28)26-18(15)27(14)11-5-4-8-25-10-11/h9,11,25H,4-5,7-8,10H2,1-2H3,(H2,23,28)(H2,24,29)/t11-/m0/s1

Standard InChI Key:  VUSIBGXJGOLGIN-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    8.4361   -5.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4402   -4.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7304   -5.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -3.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8989   -4.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6069   -4.7490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051   -3.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3138   -3.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3186   -4.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -4.5899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830   -3.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -3.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3578   -5.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124   -5.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -6.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8663   -6.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117   -6.3057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1572   -5.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -2.2944    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -2.4793    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.3969   -3.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2141   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0312   -3.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908   -4.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835   -4.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -5.5653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2612   -4.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6740   -5.3084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6656   -3.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 10  1  6
  7 19  1  0
 12 20  1  0
 21 22  3  0
 11 21  1  0
 22 23  1  0
  5 24  1  0
 24 25  2  0
 24 26  1  0
 23  2  1  0
  2 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533366

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 436.34

Molecular Weight (Monoisotopic): 435.1229

AlogP: 2.62

#Rotatable Bonds: 4

Polar Surface Area: 116.03

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.98

CX Basic pKa: 9.96

CX LogP: 2.76

CX LogD: 0.28

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: -0.41

References

1. Barberis C, Pribish J, Tserlin E, Gross A, Czekaj M, Barragué M, Erdman P, Maniar S, Jiang J, Fire L, Patel V, Hebert A, Levit M, Wang A, Sun F, Huang SA..  (2019)  Discovery of N-substituted 7-azaindoles as Pan-PIM kinases inhibitors - Lead optimization - Part III.,  29  (3): [PMID:30553737] [10.1016/j.bmcl.2018.12.015]

Source

Source(1):

• Scientific Literature