N-(4-(3-(trifluoromethyl)phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

ID: ALA3260358

Cas Number: 1362151-42-5

PubChem CID: 66613669

Max Phase: Preclinical

Molecular Formula: C21H15F3N4O3S

Molecular Weight: 460.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(S(=O)(=O)c2cccc(C(F)(F)F)c2)cc1)c1cnc2[nH]ncc2c1

Standard InChI:  InChI=1S/C21H15F3N4O3S/c22-21(23,24)16-2-1-3-18(9-16)32(30,31)17-6-4-13(5-7-17)10-26-20(29)15-8-14-12-27-28-19(14)25-11-15/h1-9,11-12H,10H2,(H,26,29)(H,25,27,28)

Standard InChI Key:  LKBHAGGICJWHQQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    8.3892  -10.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3881  -11.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0961  -11.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8058  -11.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8030  -10.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0943   -9.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6814   -9.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9738  -10.2523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2660   -9.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5584  -10.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2658   -9.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -11.4785    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2212  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0993  -12.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9165  -12.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -9.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8565  -11.4769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607  -11.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437  -11.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1411  -10.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -9.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769  -10.6616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625  -11.3252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9262  -11.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6328  -11.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6320  -10.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9187   -9.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2150  -10.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3410  -11.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3419  -12.2928    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0482  -11.0662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0450  -11.8823    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  4 12  1  0
 12 13  1  0
 12 14  2  0
 12 15  2  0
 10 16  2  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 18 10  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 13 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 13  1  0
 25 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3260358

   N-(4-{[3-(Trifluoromethyl)phenyl]sulfonyl}benzyl)-2h-Pyrazolo[3,4-B]pyridine-5-Carboxamide

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: 460.44

Molecular Weight (Monoisotopic): 460.0817

AlogP: 3.74

#Rotatable Bonds: 5

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.07

CX Basic pKa: 1.75

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -1.96

References

1. Zheng X, Bair KW, Bauer P, Baumeister T, Bowman KK, Buckmelter AJ, Caligiuri M, Clodfelter KH, Feng Y, Han B, Ho YC, Kley N, Li H, Liang X, Liederer BM, Lin J, Ly J, O'Brien T, Oeh J, Oh A, Reynolds DJ, Sampath D, Sharma G, Skelton N, Smith CC, Tremayne J, Wang L, Wang W, Wang Z, Wu H, Wu J, Xiao Y, Yang G, Yuen PW, Zak M, Dragovich PS..  (2013)  Identification of amides derived from 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT).,  23  (20): [PMID:24021463] [10.1016/j.bmcl.2013.08.074]

2. Zak M, Yuen PW, Liu X, Patel S, Sampath D, Oeh J, Liederer BM, Wang W, O'Brien T, Xiao Y, Skelton N, Hua R, Sodhi J, Wang Y, Zhang L, Zhao G, Zheng X, Ho YC, Bair KW, Dragovich PS..  (2016)  Minimizing CYP2C9 Inhibition of Exposed-Pyridine NAMPT (Nicotinamide Phosphoribosyltransferase) Inhibitors.,  59  (18): [PMID:27541271] [10.1021/acs.jmedchem.6b00697]

Source

Source(1):

• Scientific Literature