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

ID: ALA3133255

PubChem CID: 76322082

Max Phase: Preclinical

Molecular Formula: C20H18F2N2O4S

Molecular Weight: 420.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18F2N2O4S/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:  AMNQDPUKNDHUGB-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

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   30.9439  -10.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9747  -10.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7049  -11.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6393   -9.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.4021  -10.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1975  -11.0219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   34.4813  -10.3027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3696   -8.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5581  -10.1461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7677   -9.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.2559  -11.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0617  -12.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2370  -12.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8147  -13.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2171  -13.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0464  -13.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4650  -13.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1889  -12.2578    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.7956  -14.6257    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  1 15  1  0
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 18 19  1  0
 19 15  1  0
 10 20  1  0
 19 21  1  6
 20 22  1  0
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 27 22  1  0
 21 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133255

   5-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]sulfonyl-1-[(4-fluorophenyl)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: 420.44

Molecular Weight (Monoisotopic): 420.0955

AlogP: 2.68

#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: 2.40

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.52

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