3-amino-6-(difluoromethyl)-4-methyl-N-[2-(4-piperazin-1-ylphenyl)ethyl]thieno[2,3-b]pyridine-2-carboxamide

ID: ALA4514363

PubChem CID: 155539284

Max Phase: Preclinical

Molecular Formula: C22H25F2N5OS

Molecular Weight: 445.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C(F)F)nc2sc(C(=O)NCCc3ccc(N4CCNCC4)cc3)c(N)c12

Standard InChI:  InChI=1S/C22H25F2N5OS/c1-13-12-16(20(23)24)28-22-17(13)18(25)19(31-22)21(30)27-7-6-14-2-4-15(5-3-14)29-10-8-26-9-11-29/h2-5,12,20,26H,6-11,25H2,1H3,(H,27,30)

Standard InChI Key:  VKCJFWAWBORFRI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.6954   -4.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -5.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023   -5.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005   -4.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091   -4.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1144   -5.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8987   -5.5718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3772   -4.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902   -4.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1377   -3.4614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1944   -4.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -5.6041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5984   -4.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4247   -5.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8378   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6550   -6.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0619   -7.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8782   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2832   -6.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8647   -5.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0501   -5.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1004   -6.2893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5110   -6.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3246   -6.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7313   -6.2787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3183   -5.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4985   -5.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -5.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788   -5.3212    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9855   -6.5475    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980   -3.2767    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
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  6  7  1  0
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  8  9  2  0
  9  5  1  0
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  8 11  1  0
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 11 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  2 28  1  0
 28 29  1  0
 28 30  1  0
  4 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514363

   ---

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: 445.54

Molecular Weight (Monoisotopic): 445.1748

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 83.28

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.89

CX LogP: 3.67

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -1.71

References

1.  (2017)  Thienopyridine carboxamides as ubiquitin-specific protease inhibitors, 

Source

Source(1):

• Patent Bioactivity Data