3-(4-bromophenyl)-8-(2,4,6-trimethylbenzenesulfonyl)-1,4,8-triazaspiro[4.5]dec-3-en-2-one

ID: ALA5273945

Max Phase: Preclinical

Molecular Formula: C22H24BrN3O3S

Molecular Weight: 490.42

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(S(=O)(=O)N2CCC3(CC2)N=C(c2ccc(Br)cc2)C(=O)N3)c(C)c1

Standard InChI:  InChI=1S/C22H24BrN3O3S/c1-14-12-15(2)20(16(3)13-14)30(28,29)26-10-8-22(9-11-26)24-19(21(27)25-22)17-4-6-18(23)7-5-17/h4-7,12-13H,8-11H2,1-3H3,(H,25,27)

Standard InChI Key:  FEWPCIOEDOXXRX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -1.1745   -0.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -0.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -0.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -1.6673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -2.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686   -2.0797    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -1.2546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071   -0.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1766    0.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529   -0.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038   -0.8970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5890    0.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138    0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8243    1.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4118    2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5911    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    1.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956   -0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101   -0.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1116   -1.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -2.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242    2.9062    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5562   -2.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518   -2.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8243   -0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -2.9062    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
 20 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5273945

   ---

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: 490.42

Molecular Weight (Monoisotopic): 489.0722

AlogP: 3.47

#Rotatable Bonds: 3

Polar Surface Area: 78.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.98

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 5.06

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: -1.08

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