2-[2-(N-Ethylcarbamoyloxy)ethyl]-4,6-dimethylisotiazolo[5,4-b]pyridin-3(2H)-one

ID: ALA2419973

PubChem CID: 16662818

Max Phase: Preclinical

Molecular Formula: C13H17N3O3S

Molecular Weight: 295.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)OCCn1sc2nc(C)cc(C)c2c1=O

Standard InChI:  InChI=1S/C13H17N3O3S/c1-4-14-13(18)19-6-5-16-12(17)10-8(2)7-9(3)15-11(10)20-16/h7H,4-6H2,1-3H3,(H,14,18)

Standard InChI Key:  XLXFQKDKASNFHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    5.0787   -9.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367   -9.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507   -9.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -9.6960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1194   -7.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3505   -8.8710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8631   -8.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646   -8.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8631   -9.5377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787   -8.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507   -8.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1719   -8.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5836   -8.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4050   -8.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8167   -7.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6381   -7.4531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4071   -6.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0499   -6.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8712   -6.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 12  3  2  0
  8  5  2  0
  1 11  1  0
 11  9  2  0
 10  7  1  0
  9  6  1  0
  1  4  2  0
  1 10  1  0
  3  2  1  0
  9 12  1  0
  7  8  1  0
 11  8  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2419973

   2-(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)ethyl N-ethylcarbamate

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: 295.36

Molecular Weight (Monoisotopic): 295.0991

AlogP: 1.82

#Rotatable Bonds: 4

Polar Surface Area: 73.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.26

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.93

Np Likeness Score: -1.23

References

1. Malinka W, Swiątek P, Sliwińska M, Szponar B, Gamian A, Karczmarzyk Z, Fruziński A..  (2013)  Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes.,  21  (17): [PMID:23850103] [10.1016/j.bmc.2013.06.027]

2. Furdas SD, Hoffmann I, Robaa D, Herquel B, Malinka W, Swiatek P, Akhtar A, Sippl W, Jung M.  (2014)  Pyrido- and benzisothiazolones as inhibitors of histone acetyltransferases (HATs),  5  (12): [10.1039/C4MD00245H]

Source

Source(1):

• Scientific Literature