(S)-1-(4-Bromobenzyl)-5-(2-(fluoromethyl)pyrrolidin-1-ylsulfonyl)1H-indole-2,3-dione

ID: ALA3133253

PubChem CID: 76325698

Max Phase: Preclinical

Molecular Formula: C20H18BrFN2O4S

Molecular Weight: 481.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(=O)N(Cc2ccc(Br)cc2)c2ccc(S(=O)(=O)N3CCC[C@H]3CF)cc21

Standard InChI:  InChI=1S/C20H18BrFN2O4S/c21-14-5-3-13(4-6-14)12-23-18-8-7-16(10-17(18)19(25)20(23)26)29(27,28)24-9-1-2-15(24)11-22/h3-8,10,15H,1-2,9,11-12H2/t15-/m0/s1

Standard InChI Key:  GAHXAXBPTNBDFH-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   12.6592   -9.8661    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0436   -9.1361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2192   -9.1682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3890  -10.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4198  -11.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1500  -11.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0844   -9.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8150  -10.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8471  -11.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6425  -11.2421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1018  -10.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5904   -9.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9262  -10.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8145   -9.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0032  -10.3664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2130  -10.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7437  -10.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2442  -11.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0225  -11.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9291  -12.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7011  -11.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5067  -12.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6821  -12.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2597  -13.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6622  -14.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4914  -14.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9100  -13.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6340  -12.4780    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2407  -14.8457    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 11 13  2  0
 12 14  2  0
  4  1  1  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 10 20  1  0
 19 21  1  6
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 21 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133253

   1-[(4-bromophenyl)methyl]-5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonylindole-2,3-dione

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: 481.34

Molecular Weight (Monoisotopic): 480.0155

AlogP: 3.30

#Rotatable Bonds: 5

Polar Surface Area: 74.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -1.41

References

1. Krause-Heuer AM, Howell NR, Matesic L, Dhand G, Young EL, Burgess L, Jiang CD, Lengkeek NA, Fookes CJR, Pham TQ, Sobrio F, Greguric I, Fraser BH.  (2013)  A new class of fluorinated 5-pyrrolidinylsulfonyl isatin caspase inhibitors for PET imaging of apoptosis,  4  (2): [10.1039/C2MD20249B]

Source

Source(1):

• Scientific Literature