3-(4-bromophenyl)-8-(4-tert-butylbenzenesulfonyl)-1,4,8-triazaspiro[4.5]dec-3-en-2-one

ID: ALA5273722

Max Phase: Preclinical

Molecular Formula: C23H26BrN3O3S

Molecular Weight: 504.45

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)N2CCC3(CC2)N=C(c2ccc(Br)cc2)C(=O)N3)cc1

Standard InChI:  InChI=1S/C23H26BrN3O3S/c1-22(2,3)17-6-10-19(11-7-17)31(29,30)27-14-12-23(13-15-27)25-20(21(28)26-23)16-4-8-18(24)9-5-16/h4-11H,12-15H2,1-3H3,(H,26,28)

Standard InChI Key:  INBLOVOLXLHRRK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -1.5317   -0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027   -0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027   -1.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   -2.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -1.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -2.1359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3258   -1.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -1.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8643   -0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101   -0.0979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -0.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711    0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816    1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690    2.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484    2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260   -0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -0.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -0.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546   -1.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0431   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815    2.8501    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1991   -2.8501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1947   -2.7191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673   -0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    0.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1816   -0.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1816   -0.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  4  7  1  0
  7  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
  1 12  1  0
 10 13  2  0
 14 11  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 14 19  1  0
 19 18  2  0
 20  8  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
  8 24  1  0
 17 25  1  0
  7 26  2  0
  7 27  2  0
 22 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5273722

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 504.45

Molecular Weight (Monoisotopic): 503.0878

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 78.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.79

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 5.07

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -1.24

References

1. Bhuiyan AI, Choi AH, Ghoshal S, Adiele UA, Dana D, Choi JY, Fath KR, Talele TT, Pathak SK..  (2023)  Identification of a novel spirocyclic Nek2 inhibitor using high throughput virtual screening.,  88  [PMID:37094724] [10.1016/j.bmcl.2023.129288]

Source

Source(1):

• Scientific Literature