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

ID: ALA4076395

PubChem CID: 126511899

Max Phase: Preclinical

Molecular Formula: C17H14N4O3S2

Molecular Weight: 386.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc(Oc2sc(C(N)=O)c3c2-c2sncc2CC3)cn1

Standard InChI:  InChI=1S/C17H14N4O3S2/c1-19-16(23)11-5-3-9(7-20-11)24-17-12-10(14(25-17)15(18)22)4-2-8-6-21-26-13(8)12/h3,5-7H,2,4H2,1H3,(H2,18,22)(H,19,23)

Standard InChI Key:  NZIVBHCIRGQSRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    8.1797   -8.5005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212  -10.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4333  -10.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1453   -9.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1453  -10.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9267  -10.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4096   -9.9531    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9267   -9.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887   -8.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212   -9.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4333   -9.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2570   -8.3196    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4359   -8.2381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1049   -8.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1815  -11.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6294  -12.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9885  -11.5740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5353   -8.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3436   -8.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6031   -7.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0481   -7.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2419   -7.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4107   -7.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9608   -8.4427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6680   -7.0439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7684   -8.2737    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
 20 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4076395

   ---

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: 386.46

Molecular Weight (Monoisotopic): 386.0507

AlogP: 2.62

#Rotatable Bonds: 4

Polar Surface Area: 107.20

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.75

CX Basic pKa: 1.91

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.84

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