ethyl 4-{[2-(4-bromophenyl)-3-oxo-1,4,8-triazaspiro[4.5]dec-1-en-8-yl]sulfonyl}benzoate

ID: ALA5281716

Max Phase: Preclinical

Molecular Formula: C22H22BrN3O5S

Molecular Weight: 520.41

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H22BrN3O5S/c1-2-31-21(28)16-5-9-18(10-6-16)32(29,30)26-13-11-22(12-14-26)24-19(20(27)25-22)15-3-7-17(23)8-4-15/h3-10H,2,11-14H2,1H3,(H,25,27)

Standard InChI Key:  ODJBFBRQPGMUFB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.5314   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -0.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8169   -1.7234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -2.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -1.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027   -2.1357    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -1.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601   -1.3107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5785   -0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3751   -0.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6603    0.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851    0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8955    1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831    2.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624    2.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6117   -0.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0402   -1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8954    2.8499    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151   -2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4803   -2.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528   -0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528    0.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -0.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955   -0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  5  4  1  0
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  6  5  1  0
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  1  9  1  0
  9 10  1  0
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  1 12  1  0
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  8 24  1  0
 17 25  1  0
  7 26  2  0
  7 27  2  0
 22 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281716

   ---

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: 520.41

Molecular Weight (Monoisotopic): 519.0464

AlogP: 2.73

#Rotatable Bonds: 5

Polar Surface Area: 105.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.65

CX Basic pKa: ┄

CX LogP: 3.89

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: -1.10

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