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

ID: ALA4063680

PubChem CID: 126549930

Max Phase: Preclinical

Molecular Formula: C18H16N4O3S2

Molecular Weight: 400.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H16N4O3S2/c1-22(2)17(24)12-6-4-10(8-20-12)25-18-13-11(15(26-18)16(19)23)5-3-9-7-21-27-14(9)13/h4,6-8H,3,5H2,1-2H3,(H2,19,23)

Standard InChI Key:  OEHBLKFWGKSFLY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
   11.7035   -9.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  5  1  0
  4 11  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  8  4  2  0
  8  1  1  0
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 10 11  2  0
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  6 15  1  0
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 15 17  1  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
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 20 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063680

   ---

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: 400.49

Molecular Weight (Monoisotopic): 400.0664

AlogP: 2.96

#Rotatable Bonds: 4

Polar Surface Area: 98.41

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 1.90

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -1.01

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