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

ID: ALA3133146

PubChem CID: 76314800

Max Phase: Preclinical

Molecular Formula: C20H18FN3O6S

Molecular Weight: 447.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(=O)N(Cc2ccccc2[N+](=O)[O-])c2ccc(S(=O)(=O)N3CCC[C@H]3CF)cc21

Standard InChI:  InChI=1S/C20H18FN3O6S/c21-11-14-5-3-9-23(14)31(29,30)15-7-8-18-16(10-15)19(25)20(26)22(18)12-13-4-1-2-6-17(13)24(27)28/h1-2,4,6-8,10,14H,3,5,9,11-12H2/t14-/m0/s1

Standard InChI Key:  ABCKZNSVBLCRMS-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   11.8682  -24.8832    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2526  -24.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4282  -24.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5981  -25.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6289  -26.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3592  -26.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2935  -24.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0242  -25.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0564  -26.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8517  -26.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3112  -25.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7996  -24.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1355  -25.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0239  -24.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2123  -25.3836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4219  -25.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9527  -25.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4531  -26.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2315  -26.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1384  -27.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9101  -26.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7159  -27.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8913  -27.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4689  -28.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8715  -29.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7006  -29.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1193  -28.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8432  -27.4953    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9495  -28.4621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3688  -27.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3554  -29.1804    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
  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
 29 30  2  0
 29 31  1  0
 27 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3133146

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(2-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: -1.59

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