8-[(2-Methylpyridin-3-yl)oxy]-4,5-dihydrothieno[3,4-g][1,2]benzisothiazole-6-carboxamide

ID: ALA4070408

PubChem CID: 126511887

Max Phase: Preclinical

Molecular Formula: C16H13N3O2S2

Molecular Weight: 343.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncccc1Oc1sc(C(N)=O)c2c1-c1sncc1CC2

Standard InChI:  InChI=1S/C16H13N3O2S2/c1-8-11(3-2-6-18-8)21-16-12-10(14(22-16)15(17)20)5-4-9-7-19-23-13(9)12/h2-3,6-7H,4-5H2,1H3,(H2,17,20)

Standard InChI Key:  AIRVMUGRIFXGRE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    7.4380   -6.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795   -7.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916   -8.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -7.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -7.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -8.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679   -7.5321    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1850   -6.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2470   -5.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795   -7.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916   -6.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153   -5.8987    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -5.8172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3632   -6.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399   -8.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8877   -9.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2468   -9.1531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7936   -6.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6019   -6.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8614   -5.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3065   -4.9580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5002   -5.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9479   -4.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  2  1  0
  2  3  1  0
  3  5  1  0
  4 11  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  8  1  1  0
  1  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  6 15  1  0
 15 16  2  0
 15 17  1  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  9  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4070408

   ---

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: 343.43

Molecular Weight (Monoisotopic): 343.0449

AlogP: 3.56

#Rotatable Bonds: 3

Polar Surface Area: 78.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 5.47

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.67

References

1. Ono K, Banno H, Okaniwa M, Hirayama T, Iwamura N, Hikichi Y, Murai S, Hasegawa M, Hasegawa Y, Yonemori K, Hata A, Aoyama K, Cary DR..  (2017)  Design and synthesis of selective CDK8/19 dual inhibitors: Discovery of 4,5-dihydrothieno[3',4':3,4]benzo[1,2-d]isothiazole derivatives.,  25  (8): [PMID:28302507] [10.1016/j.bmc.2017.02.038]

Source

Source(1):

• Scientific Literature