4-(4-Methoxyphenyl)-4-(2,2,2-trifluoroethoxy)-4H-[1,2,4]-oxadiazolo[3,4-c][1,4]benzothiazin-1-one

ID: ALA3819349

PubChem CID: 127052464

Max Phase: Preclinical

Molecular Formula: C18H13F3N2O4S

Molecular Weight: 410.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(OCC(F)(F)F)Sc3ccccc3-n3c2noc3=O)cc1

Standard InChI:  InChI=1S/C18H13F3N2O4S/c1-25-12-8-6-11(7-9-12)18(26-10-17(19,20)21)15-22-27-16(24)23(15)13-4-2-3-5-14(13)28-18/h2-9H,10H2,1H3

Standard InChI Key:  AWBSGIHJNCVFLA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.9460   -1.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426   -2.0562    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426    0.8996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9547    2.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601    2.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    1.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496    3.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -2.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -0.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -3.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -5.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703   -5.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016   -5.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605   -3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609   -1.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460   -2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678   -1.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083   -7.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456   -7.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5460   -1.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797   -1.0969    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8428    0.1024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.6702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 17  2  1  0
 16  4  1  0
  3  1  1  0
  1  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  2  0
  5  8  2  0
  1  9  1  0
  1 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 22  1  0
 22 23  1  0
 10 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3819349

   ---

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: 410.37

Molecular Weight (Monoisotopic): 410.0548

AlogP: 3.72

#Rotatable Bonds: 4

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.94

References

1. Carosati E, Cosimelli B, Ioan P, Severi E, Katneni K, Chiu FC, Saponara S, Fusi F, Frosini M, Matucci R, Micucci M, Chiarini A, Spinelli D, Budriesi R..  (2016)  Understanding Oxadiazolothiazinone Biological Properties: Negative Inotropic Activity versus Cytochrome P450-Mediated Metabolism.,  59  (7): [PMID:26962886] [10.1021/acs.jmedchem.6b00030]

Source

Source(1):

• Scientific Literature