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

ID: ALA3133256

PubChem CID: 76311201

Max Phase: Preclinical

Molecular Formula: C20H18FIN2O4S

Molecular Weight: 528.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(=O)N(Cc2ccccc2I)c2ccc(S(=O)(=O)N3CCC[C@H]3CF)cc21

Standard InChI:  InChI=1S/C20H18FIN2O4S/c21-11-14-5-3-9-24(14)29(27,28)15-7-8-18-16(10-15)19(25)20(26)23(18)12-13-4-1-2-6-17(13)22/h1-2,4,6-8,10,14H,3,5,9,11-12H2/t14-/m0/s1

Standard InChI Key:  VZUJUIONFIJSIE-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.7305  -17.1406    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149  -16.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2905  -16.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4605  -17.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912  -18.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214  -18.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558  -17.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8864  -17.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186  -18.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7138  -18.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1733  -17.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6618  -17.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9976  -17.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8860  -16.3867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0746  -17.6409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2843  -17.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8151  -18.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3155  -18.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938  -18.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0005  -19.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7724  -18.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5781  -19.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535  -19.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3311  -20.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336  -21.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5628  -21.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9814  -20.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055  -19.7525    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8063  -20.7195    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
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133256

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(2-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: -1.39

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