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

ID: ALA3133257

PubChem CID: 76314804

Max Phase: Preclinical

Molecular Formula: C20H18FIN2O4S

Molecular Weight: 528.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18FIN2O4S/c21-11-15-5-2-8-24(15)29(27,28)16-6-7-18-17(10-16)19(25)20(26)23(18)12-13-3-1-4-14(22)9-13/h1,3-4,6-7,9-10,15H,2,5,8,11-12H2/t15-/m0/s1

Standard InChI Key:  CGZTYJDMCMAZBO-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.4890  -17.1708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8735  -16.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0491  -16.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2189  -17.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2497  -18.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9800  -18.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9143  -17.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6450  -17.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6772  -18.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4726  -18.5469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9320  -17.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4205  -17.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7563  -17.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6447  -16.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8331  -17.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0427  -17.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5735  -18.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0739  -18.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -18.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7593  -19.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5309  -18.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3368  -20.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5121  -20.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0898  -20.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4923  -21.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3214  -21.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7401  -20.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4640  -19.7828    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.7265  -22.1693    0.0000 I   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
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133257

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(3-iodophenyl)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: 528.34

Molecular Weight (Monoisotopic): 528.0016

AlogP: 3.14

#Rotatable Bonds: 5

Polar Surface Area: 74.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.66

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