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

ID: ALA3133147

PubChem CID: 76311196

Max Phase: Preclinical

Molecular Formula: C20H18FN3O6S

Molecular Weight: 447.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(=O)N(Cc2cccc([N+](=O)[O-])c2)c2ccc(S(=O)(=O)N3CCC[C@H]3CF)cc21

Standard InChI:  InChI=1S/C20H18FN3O6S/c21-11-15-5-2-8-23(15)31(29,30)16-6-7-18-17(10-16)19(25)20(26)22(18)12-13-3-1-4-14(9-13)24(27)28/h1,3-4,6-7,9-10,15H,2,5,8,11-12H2/t15-/m0/s1

Standard InChI Key:  ZSLCIFACVMMVCF-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   21.5515  -24.8208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9360  -24.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1116  -24.1228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2814  -25.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3122  -26.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0424  -26.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9768  -24.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7075  -25.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7396  -25.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5350  -26.1969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9945  -25.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4830  -24.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8188  -25.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7071  -24.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8955  -25.3211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1052  -25.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6360  -25.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1364  -26.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9148  -26.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8217  -26.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5934  -26.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3993  -27.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5746  -27.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1523  -28.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5547  -29.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3839  -29.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8026  -28.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5265  -27.4328    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.7906  -29.8221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6155  -29.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3706  -30.5322    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
 26 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3133147

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(3-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: -1.73

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