4-(Cyclohexylmethoxy)-4-phenyl-4H-[1,2,4]oxadiazolo[3,4-c]-[1,4]benzothiazin-1-one

ID: ALA3818275

PubChem CID: 127051286

Max Phase: Preclinical

Molecular Formula: C22H22N2O3S

Molecular Weight: 394.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1onc2n1-c1ccccc1SC2(OCC1CCCCC1)c1ccccc1

Standard InChI:  InChI=1S/C22H22N2O3S/c25-21-24-18-13-7-8-14-19(18)28-22(20(24)23-27-21,17-11-5-2-6-12-17)26-15-16-9-3-1-4-10-16/h2,5-8,11-14,16H,1,3-4,9-10,15H2

Standard InChI Key:  MLBBYHYNDPKELT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  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
    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
    7.1451   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193   -0.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3709    1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0484    1.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    0.9701    0.0000 C   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
 10 22  1  0
 22 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818275

   ---

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: 394.50

Molecular Weight (Monoisotopic): 394.1351

AlogP: 4.73

#Rotatable Bonds: 4

Polar Surface Area: 57.26

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.36

CX LogD: 6.36

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.63

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