US8987314, B63

ID: ALA3672653

PubChem CID: 89969715

Max Phase: Preclinical

Molecular Formula: C20H23N3O6S3

Molecular Weight: 497.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCc1ccc(-c2ccc3nc(C(C(=O)NCCS(N)(=O)=O)S(C)(=O)=O)sc3c2)cc1

Standard InChI:  InChI=1S/C20H23N3O6S3/c1-29-12-13-3-5-14(6-4-13)15-7-8-16-17(11-15)30-20(23-16)18(31(2,25)26)19(24)22-9-10-32(21,27)28/h3-8,11,18H,9-10,12H2,1-2H3,(H,22,24)(H2,21,27,28)

Standard InChI Key:  LRHPOJWPSLDDRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    7.5241   -5.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4870   -5.2605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   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
    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
   -2.7248    1.2135    0.0000 N   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 S   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  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 17 18  2  0
 18 10  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 19 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3672653

   2-[6-[4-(methoxymethyl)phenyl]-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: 497.62

Molecular Weight (Monoisotopic): 497.0749

AlogP: 1.60

#Rotatable Bonds: 9

Polar Surface Area: 145.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 0.47

CX LogD: 0.21

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.29

References

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

Source

Source(1):

• BindingDB Database