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

ID: ALA5284785

Max Phase: Preclinical

Molecular Formula: C19H18BrN3O3S

Molecular Weight: 448.34

Names and Identifiers

Canonical SMILES:  O=C1NC2(CCN(S(=O)(=O)c3ccccc3)CC2)N=C1c1ccc(Br)cc1

Standard InChI:  InChI=1S/C19H18BrN3O3S/c20-15-8-6-14(7-9-15)17-18(24)22-19(21-17)10-12-23(13-11-19)27(25,26)16-4-2-1-3-5-16/h1-9H,10-13H2,(H,22,24)

Standard InChI Key:  RYMXZGZXOABCOY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.1037   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107   -0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107   -1.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -2.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182   -1.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -2.1359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -1.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418   -2.7191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374   -2.8501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324   -1.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508   -0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -0.0979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475   -0.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681    1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    2.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8186    1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    2.8501    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0395   -0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7520   -0.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666   -0.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681   -1.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  3  1  0
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  7  8  1  0
  7  9  2  0
  7 10  2  0
  1 11  1  0
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  1 14  1  0
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 17 16  2  0
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 16 21  1  0
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 26 25  1  0
 27 26  2  0
  8 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284785

   ---

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: 448.34

Molecular Weight (Monoisotopic): 447.0252

AlogP: 2.55

#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: 9.83

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -1.22

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