(S)-N-(4-Fluorobutyl)-7-chloro-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin

ID: ALA3359200

PubChem CID: 118723328

Max Phase: Preclinical

Molecular Formula: C17H20ClFN2O5S

Molecular Weight: 418.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@@H]1CCCN1S(=O)(=O)c1cc(Cl)c2c(c1)C(=O)C(=O)N2CCCF

Standard InChI:  InChI=1S/C17H20ClFN2O5S/c1-26-10-11-4-2-7-21(11)27(24,25)12-8-13-15(14(18)9-12)20(6-3-5-19)17(23)16(13)22/h8-9,11H,2-7,10H2,1H3/t11-/m0/s1

Standard InChI Key:  AEYFPXLRNOQPNR-NSHDSACASA-N

Molfile:  

     RDKit          2D

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    2.6332  -26.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0459  -27.0705    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543  -26.3581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7544  -27.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532  -28.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613  -28.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4595  -27.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681  -27.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1684  -28.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9470  -28.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4280  -27.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9466  -27.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2452  -27.8841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1988  -26.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389  -27.4794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970  -27.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0504  -27.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4592  -28.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584  -28.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8673  -28.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6998  -29.6344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234  -29.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634  -29.5247    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1998  -29.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531  -29.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059  -30.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7052  -30.8782    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
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 11 13  2  0
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  4  2  1  0
  2 15  1  0
 15 16  1  0
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 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
 10 24  1  0
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 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359200

   ---

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: 418.87

Molecular Weight (Monoisotopic): 418.0765

AlogP: 2.03

#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: 1.15

CX LogD: 1.15

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.29

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