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

ID: ALA3133258

PubChem CID: 76318413

Max Phase: Preclinical

Molecular Formula: C20H18FIN2O4S

Molecular Weight: 528.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18FIN2O4S/c21-11-15-2-1-9-24(15)29(27,28)16-7-8-18-17(10-16)19(25)20(26)23(18)12-13-3-5-14(22)6-4-13/h3-8,10,15H,1-2,9,11-12H2/t15-/m0/s1

Standard InChI Key:  JQQCMQLLJHRXIA-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

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   22.0725  -17.0792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4569  -16.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6325  -16.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8024  -17.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8332  -18.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5634  -18.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4978  -17.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2285  -17.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2606  -18.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0560  -18.4553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5155  -17.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0039  -17.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3398  -17.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2280  -16.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4166  -17.5795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6262  -17.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1569  -18.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6574  -18.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4357  -18.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3426  -19.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1144  -18.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9202  -19.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0955  -19.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6732  -20.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0756  -21.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9049  -21.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3235  -20.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0474  -19.6912    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.6541  -22.0591    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
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133258

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(4-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: -1.58

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