3-(4-(2,6-difluoro-4-methoxyphenylsulfonyl)piperazin-1-ylsulfonyl)aniline

ID: ALA1091760

PubChem CID: 44543606

Max Phase: Preclinical

Molecular Formula: C17H19F2N3O5S2

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(F)c(S(=O)(=O)N2CCN(S(=O)(=O)c3cccc(N)c3)CC2)c(F)c1

Standard InChI:  InChI=1S/C17H19F2N3O5S2/c1-27-13-10-15(18)17(16(19)11-13)29(25,26)22-7-5-21(6-8-22)28(23,24)14-4-2-3-12(20)9-14/h2-4,9-11H,5-8,20H2,1H3

Standard InChI Key:  NZIGHJSJPVTZFS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.3312   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2687   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2687    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3312    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    1.4289    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563   -1.4289    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  6  7  1  0
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  8 10  2  0
 11 12  1  0
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 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 16  1  0
  8 11  1  0
 17 18  2  0
 17 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 17 20  1  0
 26 27  1  0
 23 26  1  0
 25 28  1  0
 21 29  1  0
 14 17  1  0
  4  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091760

   3-[4-(2,6-Difluoro-4-methoxyphenyl)sulfonylpiperazin-1-yl]sulfonylaniline

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: 447.49

Molecular Weight (Monoisotopic): 447.0734

AlogP: 1.25

#Rotatable Bonds: 5

Polar Surface Area: 110.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.21

CX LogP: 1.01

CX LogD: 1.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.44

References

1. Boxer MB, Jiang JK, Vander Heiden MG, Shen M, Skoumbourdis AP, Southall N, Veith H, Leister W, Austin CP, Park HW, Inglese J, Cantley LC, Auld DS, Thomas CJ..  (2010)  Evaluation of substituted N,N'-diarylsulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase.,  53  (3): [PMID:20017496] [10.1021/jm901577g]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays