US8987314, B193

ID: ALA3677528

PubChem CID: 89962855

Max Phase: Preclinical

Molecular Formula: C17H17FN4O6S3

Molecular Weight: 488.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)C(C(=O)NCCS(N)(=O)=O)c1nc2ccc(-c3ccnc(O)c3F)cc2s1

Standard InChI:  InChI=1S/C17H17FN4O6S3/c1-30(25,26)14(16(24)21-6-7-31(19,27)28)17-22-11-3-2-9(8-12(11)29-17)10-4-5-20-15(23)13(10)18/h2-5,8,14H,6-7H2,1H3,(H,20,23)(H,21,24)(H2,19,27,28)

Standard InChI Key:  MLXSPNNQONOVKU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.2505   -4.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505   -4.4281    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -5.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -3.3910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -5.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974   -5.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -7.0223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -8.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405   -9.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882  -10.9210    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3861  -11.9615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882  -10.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862  -11.9591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    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
    0.3114   -2.9665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9014    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    4.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    3.6021    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 23 15  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 24  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3677528

   2-[6-(3-fluoro-2-oxo-1H-pyridin-4-yl)-1,3-benzothiazol-2-yl]-2-methylsulfonyl-N-(2-sulfamoylethyl)acetamide

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: 488.54

Molecular Weight (Monoisotopic): 488.0294

AlogP: 0.69

#Rotatable Bonds: 7

Polar Surface Area: 169.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.48

CX Basic pKa: 0.77

CX LogP: -0.19

CX LogD: -0.45

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -1.34

References

1.  (2015)  Amide, urea or sulfone amide linked benzothiazole inhibitors of endothelial lipase, 

Source

Source(1):

• BindingDB Database