2-(6-aminobenzo[d]thiazol-2-ylthio)-N-(5-(3-methylbenzylthio)-1,3,4-thiadiazol-2-yl)acetamide

ID: ALA3352902

PubChem CID: 3948652

Max Phase: Preclinical

Molecular Formula: C19H17N5OS4

Molecular Weight: 459.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(CSc2nnc(NC(=O)CSc3nc4ccc(N)cc4s3)s2)c1

Standard InChI:  InChI=1S/C19H17N5OS4/c1-11-3-2-4-12(7-11)9-26-19-24-23-17(29-19)22-16(25)10-27-18-21-14-6-5-13(20)8-15(14)28-18/h2-8H,9-10,20H2,1H3,(H,22,23,25)

Standard InChI Key:  VEYFCRPXPCFIFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    0.0357   -5.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -5.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -6.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408   -4.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -5.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4497   -5.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2327   -6.0842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -5.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323   -4.7523    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5336   -5.4177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424   -6.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1685   -6.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680   -5.4172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -5.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4633   -6.0786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2404   -5.8258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2402   -5.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -4.7564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9011   -4.5279    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6478   -4.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3087   -4.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0541   -4.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7146   -4.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6292   -3.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776   -3.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2202   -3.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4612   -4.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734   -4.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 24 28  1  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3352902

   2-[(6-amino-1,3-benzothiazol-2-yl)sulfanyl]-N-{5-[(3-methylbenzyl)sulfanyl]-1,3,4-thiadiazol-2-yl}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: 459.65

Molecular Weight (Monoisotopic): 459.0316

AlogP: 5.06

#Rotatable Bonds: 7

Polar Surface Area: 93.79

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.84

CX Basic pKa: 2.80

CX LogP: 5.10

CX LogD: 4.51

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: -2.79

References

1. Hou X, Li R, Li K, Yu X, Sun JP, Fang H..  (2014)  Fast identification of novel lymphoid tyrosine phosphatase inhibitors using target-ligand interaction-based virtual screening.,  57  (22): [PMID:25372368] [10.1021/jm500692u]

Source

Source(1):

• Scientific Literature