3-(1-cyanocyclopropyl)-5-(3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)phenethyl acetate

ID: ALA3310282

PubChem CID: 118706403

Max Phase: Preclinical

Molecular Formula: C21H17F3N4O2

Molecular Weight: 414.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCCc1cc(-c2ccnc3[nH]nc(C(F)(F)F)c23)cc(C2(C#N)CC2)c1

Standard InChI:  InChI=1S/C21H17F3N4O2/c1-12(29)30-7-3-13-8-14(10-15(9-13)20(11-25)4-5-20)16-2-6-26-19-17(16)18(27-28-19)21(22,23)24/h2,6,8-10H,3-5,7H2,1H3,(H,26,27,28)

Standard InChI Key:  NTZWMHHDVBAIDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   14.0605  -12.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6542  -12.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4714  -12.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9345   -8.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9334   -9.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6414   -9.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6396   -8.0354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6431  -10.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9337  -10.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9331  -11.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6413  -12.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3514  -11.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3485  -10.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2251  -12.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5177  -11.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7668  -11.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4716  -11.2897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3483   -8.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3485   -9.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1315   -9.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6152   -8.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1311   -8.1861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3842  -10.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8376  -10.9026    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.1836  -10.4648    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.5939  -11.0816    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5183  -10.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8109  -10.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8115   -9.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1029  -10.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6 19  2  0
 18  7  2  0
  7  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6  8  1  0
 10 14  1  0
 14 15  1  0
 12  1  1  0
  1 16  1  0
 16 17  3  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 15 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3310282

   ---

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: 414.39

Molecular Weight (Monoisotopic): 414.1304

AlogP: 4.30

#Rotatable Bonds: 5

Polar Surface Area: 91.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.63

Np Likeness Score: -0.36

References

1. Clemens JJ, Coon T, Busch BB, Asgian JL, Hudson S, Termin A, Flores TB, Tran D, Chiang P, Sperry S, Gross R, Abt J, Heim R, Lechner S, Twin H, Studley J, Brenchley G, Collier PN, Pierard F, Miller A, Mak C, Dvornikovs V, Jimenez JM, Stamos D..  (2014)  Strategies for the modulation of phase II metabolism in a series of PKCε inhibitors.,  24  (15): [PMID:24939756] [10.1016/j.bmcl.2014.05.082]

Source

Source(1):

• Scientific Literature