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

ID: ALA3133251

PubChem CID: 76336535

Max Phase: Preclinical

Molecular Formula: C22H22F2N2O5S

Molecular Weight: 464.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H22F2N2O5S/c23-9-11-31-17-5-3-15(4-6-17)14-25-20-8-7-18(12-19(20)21(27)22(25)28)32(29,30)26-10-1-2-16(26)13-24/h3-8,12,16H,1-2,9-11,13-14H2/t16-/m0/s1

Standard InChI Key:  ODDLUJFKRBXEAV-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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   30.6224   -1.9333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0068   -1.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1825   -1.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3524   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3832   -3.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1134   -3.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0478   -1.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7784   -2.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8106   -3.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6060   -3.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0654   -2.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9665   -2.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9858   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8927   -4.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6644   -3.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4703   -4.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6456   -4.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2232   -5.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6257   -6.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4549   -6.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8736   -5.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5974   -4.5453    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.2042   -6.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3793   -6.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9577   -7.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1328   -7.6016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  2  0
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  8  9  1  0
  9 10  1  0
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  4  1  1  0
  1 15  1  0
 15 16  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
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3133251

   1-[[4-(2-fluoroethoxy)phenyl]methyl]-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: 464.49

Molecular Weight (Monoisotopic): 464.1217

AlogP: 2.89

#Rotatable Bonds: 8

Polar Surface Area: 83.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -1.31

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