(S)-N-Butyl-7-chloro-5-[1-(2-methoxymethylpyrrolidinyl)-sulfonyl]isatin

ID: ALA3359199

PubChem CID: 118723327

Max Phase: Preclinical

Molecular Formula: C18H23ClN2O5S

Molecular Weight: 414.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1C(=O)C(=O)c2cc(S(=O)(=O)N3CCC[C@H]3COC)cc(Cl)c21

Standard InChI:  InChI=1S/C18H23ClN2O5S/c1-3-4-7-20-16-14(17(22)18(20)23)9-13(10-15(16)19)27(24,25)21-8-5-6-12(21)11-26-2/h9-10,12H,3-8,11H2,1-2H3/t12-/m0/s1

Standard InChI Key:  JLXZUACSFOZXOH-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

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   30.7933  -21.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2060  -21.8000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.6144  -21.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9144  -22.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9133  -23.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6213  -23.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6196  -21.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3282  -22.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3284  -23.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1071  -23.2764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5881  -22.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1067  -21.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4053  -22.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3589  -21.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4990  -22.2089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7571  -21.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2104  -22.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6192  -23.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4185  -23.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0274  -23.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8599  -24.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0835  -24.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6235  -24.2543    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.3598  -24.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8132  -24.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0659  -25.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5193  -26.0455    0.0000 C   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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  9 10  1  0
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 11 13  2  0
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  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
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  6 23  1  0
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 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359199

   ---

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: 414.91

Molecular Weight (Monoisotopic): 414.1016

AlogP: 2.47

#Rotatable Bonds: 7

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: 2.22

CX LogD: 2.22

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -1.19

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