Pyridine-3-sulfonic acid (3-(5-(2,6-difluoro-3-hydroxybenzoyl)-thiophene-2-yl)-phenyl)amide

ID: ALA3629588

PubChem CID: 122194413

Max Phase: Preclinical

Molecular Formula: C22H14F2N2O4S2

Molecular Weight: 472.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2cccc(NS(=O)(=O)c3cccnc3)c2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C22H14F2N2O4S2/c23-16-6-7-17(27)21(24)20(16)22(28)19-9-8-18(31-19)13-3-1-4-14(11-13)26-32(29,30)15-5-2-10-25-12-15/h1-12,26-27H

Standard InChI Key:  NSJGLJWRPZGJSH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4020  -12.0971    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0271  -11.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6837  -10.7794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4469   -5.2297    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6532   -3.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7488   -8.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649   -9.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644   -9.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7478   -8.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0317   -6.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6208  -13.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396  -14.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588  -15.9759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592  -15.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405  -14.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212  -13.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
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  9 10  2  0
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  6 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  2  0
 12 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 24 19  1  0
 15 19  1  0
 21  4  1  0
  9 25  1  0
  5 26  1  0
  4  2  1  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3629588

   ---

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: 472.49

Molecular Weight (Monoisotopic): 472.0363

AlogP: 4.83

#Rotatable Bonds: 6

Polar Surface Area: 96.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.00

CX Basic pKa: 1.07

CX LogP: 4.24

CX LogD: 3.68

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.52

References

1. Abdelsamie AS, Bey E, Gargano EM, van Koppen CJ, Empting M, Frotscher M..  (2015)  Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme.,  103  [PMID:26322835] [10.1016/j.ejmech.2015.08.030]

Source

Source(1):

• Scientific Literature