(S)-N-(1-cyanoethyl)-3-(5-(4-((tetrahydro-2H-pyran-4-ylamino)methyl)phenyl)isoxazol-3-yl)benzamide

ID: ALA1683441

PubChem CID: 53320224

Max Phase: Preclinical

Molecular Formula: C25H26N4O3

Molecular Weight: 430.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](C#N)NC(=O)c1cccc(-c2cc(-c3ccc(CNC4CCOCC4)cc3)on2)c1

Standard InChI:  InChI=1S/C25H26N4O3/c1-17(15-26)28-25(30)21-4-2-3-20(13-21)23-14-24(32-29-23)19-7-5-18(6-8-19)16-27-22-9-11-31-12-10-22/h2-8,13-14,17,22,27H,9-12,16H2,1H3,(H,28,30)/t17-/m0/s1

Standard InChI Key:  LSEXYAQECWMUPY-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    2.2849  -16.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751  -17.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851  -17.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054  -17.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7112  -16.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006  -15.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4321  -15.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287  -16.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957  -15.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1851  -14.8128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128  -15.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5201  -15.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9253  -16.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7531  -16.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759  -15.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7694  -14.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9429  -14.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1967  -14.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0253  -14.0662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7883  -13.3440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4354  -14.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565  -17.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8471  -17.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285  -17.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773  -17.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938  -17.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3073  -18.3156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982  -18.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245  -18.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0206  -15.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6076  -16.2082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2600  -14.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 15 16  1  0
  3  4  2  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
  4  5  1  0
 18 19  1  0
  2  3  1  0
 18 20  2  0
  8  9  1  0
 21 19  1  0
  9 10  2  0
  2 22  1  0
 10 11  1  0
 22 23  1  0
 11  7  1  0
 23 24  1  0
 24 25  1  0
  5  6  2  0
  9 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 13 14  1  0
 21 30  1  0
  5  7  1  0
 30 31  3  0
 14 15  2  0
 21 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1683441

   (S)-N-(1-cyanoethyl)-3-(5-(4-((tetrahydro-2H-pyran-4-ylamino)methyl)phenyl)isoxazol-3-yl)benzamide

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: 430.51

Molecular Weight (Monoisotopic): 430.2005

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 100.18

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.34

CX LogP: 2.64

CX LogD: 0.71

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -1.19

References

1. Gamber GG, Meredith E, Zhu Q, Yan W, Rao C, Capparelli M, Burgis R, Enyedy I, Zhang JH, Soldermann N, Beattie K, Rozhitskaya O, Koch KA, Pagratis N, Hosagrahara V, Vega RB, McKinsey TA, Monovich L..  (2011)  3,5-diarylazoles as novel and selective inhibitors of protein kinase D.,  21  (5): [PMID:21300545] [10.1016/j.bmcl.2011.01.014]

Source

Source(1):

• Scientific Literature