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

ID: ALA3133252

PubChem CID: 76336536

Max Phase: Preclinical

Molecular Formula: C20H19FN2O4S

Molecular Weight: 402.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H19FN2O4S/c21-12-15-7-4-10-23(15)28(26,27)16-8-9-18-17(11-16)19(24)20(25)22(18)13-14-5-2-1-3-6-14/h1-3,5-6,8-9,11,15H,4,7,10,12-13H2/t15-/m0/s1

Standard InChI Key:  HBEKNGSODXFMMQ-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

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    2.7866   -9.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9565  -10.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873  -11.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7175  -11.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -9.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825  -10.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147  -11.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2100  -11.3677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695  -10.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579  -10.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4939  -10.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3822   -9.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706  -10.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802  -10.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110  -10.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114  -11.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5898  -11.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967  -12.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684  -11.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0742  -12.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2496  -12.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8273  -13.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2298  -14.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0590  -14.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776  -13.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015  -12.6036    0.0000 F   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
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  7  4  1  0
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  9 10  1  0
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 11 13  2  0
 12 14  2  0
  4  1  1  0
  1 15  1  0
 15 16  1  0
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 18 19  1  0
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 10 20  1  0
 19 21  1  6
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 22 23  2  0
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 25 26  1  0
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 27 22  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133252

   1-benzyl-5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonylindole-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: 402.45

Molecular Weight (Monoisotopic): 402.1050

AlogP: 2.54

#Rotatable Bonds: 5

Polar Surface Area: 74.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -1.37

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