US8987314, B88

ID: ALA3677434

PubChem CID: 89962144

Max Phase: Preclinical

Molecular Formula: C18H20N4O6S3

Molecular Weight: 484.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2ccc3sc(C(C(=O)NCCS(N)(=O)=O)S(C)(=O)=O)nc3c2)ccn1

Standard InChI:  InChI=1S/C18H20N4O6S3/c1-28-15-10-12(5-6-20-15)11-3-4-14-13(9-11)22-18(29-14)16(30(2,24)25)17(23)21-7-8-31(19,26)27/h3-6,9-10,16H,7-8H2,1-2H3,(H,21,23)(H2,19,26,27)

Standard InChI Key:  XEINGMYRSNNYPB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    7.5368   -1.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994   -0.7589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   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
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    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
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   -2.7248    1.2135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8532   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2514   -2.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3541   -1.3071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1026   -2.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6034   -2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3519   -3.9119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5519   -3.9144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9499   -4.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7501   -4.9501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8601    1.2937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0601    1.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    2.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2637    2.3351    0.0000 C   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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 16 17  2  0
 17  9  1  0
 14 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 24 27  1  0
 18 28  1  0
 28 29  2  0
 28 30  2  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3677434

   2-[5-(2-methoxypyridin-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: 484.58

Molecular Weight (Monoisotopic): 484.0545

AlogP: 0.86

#Rotatable Bonds: 8

Polar Surface Area: 158.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.48

CX Basic pKa: 2.90

CX LogP: -0.18

CX LogD: -0.45

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -1.52

References

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

Source

Source(1):

• BindingDB Database