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

ID: ALA3133148

PubChem CID: 76332916

Max Phase: Preclinical

Molecular Formula: C20H18FN3O6S

Molecular Weight: 447.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18FN3O6S/c21-11-15-2-1-9-23(15)31(29,30)16-7-8-18-17(10-16)19(25)20(26)22(18)12-13-3-5-14(6-4-13)24(27)28/h3-8,10,15H,1-2,9,11-12H2/t15-/m0/s1

Standard InChI Key:  XKFNXVGANVXVEU-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

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   32.1598  -24.9583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.5442  -24.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7198  -24.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8897  -25.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9206  -26.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6508  -26.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5851  -24.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3158  -25.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3480  -26.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1433  -26.3344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6028  -25.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0912  -24.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4271  -25.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3155  -24.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5039  -25.4586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7135  -25.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2443  -25.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7447  -26.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5231  -26.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4300  -27.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2017  -26.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0075  -27.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1829  -27.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7605  -28.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1630  -29.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9922  -29.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4109  -28.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1348  -27.5703    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.7430  -29.9425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1464  -30.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9181  -29.9320    0.0000 O   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
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  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
 29 30  2  0
 29 31  1  0
 25 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3133148

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(4-nitrophenyl)methyl]indole-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: 447.44

Molecular Weight (Monoisotopic): 447.0900

AlogP: 2.45

#Rotatable Bonds: 6

Polar Surface Area: 117.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.55

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