(S)-7-Fluoro-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-isatin

ID: ALA3359201

PubChem CID: 118723329

Max Phase: Preclinical

Molecular Formula: C14H15FN2O5S

Molecular Weight: 342.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@@H]1CCCN1S(=O)(=O)c1cc(F)c2c(c1)C(=O)C(=O)N2

Standard InChI:  InChI=1S/C14H15FN2O5S/c1-22-7-8-3-2-4-17(8)23(20,21)9-5-10-12(11(15)6-9)16-14(19)13(10)18/h5-6,8H,2-4,7H2,1H3,(H,16,18,19)/t8-/m0/s1

Standard InChI Key:  WAAQKRMBGFIDTJ-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.9095  -26.7156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3222  -27.4254    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7306  -26.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0307  -27.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0295  -28.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7376  -29.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7358  -27.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4444  -27.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4447  -28.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2233  -28.9018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7043  -28.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2229  -27.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5215  -28.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4751  -26.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6152  -27.8343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8733  -27.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3267  -28.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7355  -28.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5347  -28.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1436  -29.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9761  -29.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1997  -30.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7397  -29.8797    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  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  2  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 19 20  1  6
 20 21  1  0
 21 22  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359201

   ---

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: 342.35

Molecular Weight (Monoisotopic): 342.0686

AlogP: 0.76

#Rotatable Bonds: 4

Polar Surface Area: 92.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: 1.16

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.82

Np Likeness Score: -0.99

References

1. Limpachayaporn P, Wagner S, Kopka K, Schober O, Schäfers M, Haufe G..  (2014)  Synthesis of 7-halogenated isatin sulfonamides: nonradioactive counterparts of caspase-3/-7 inhibitor-based potential radiopharmaceuticals for molecular imaging of apoptosis.,  57  (22): [PMID:25358116] [10.1021/jm500718e]

Source

Source(1):

• Scientific Literature