6-chloro-3-[1-(3-chlorophenyl)cyclobutylamino]-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide

ID: ALA383992

PubChem CID: 135467082

Max Phase: Preclinical

Molecular Formula: C15H13Cl2N3O2S2

Molecular Weight: 402.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)N=C(NC2(c3cccc(Cl)c3)CCC2)Nc2cc(Cl)sc21

Standard InChI:  InChI=1S/C15H13Cl2N3O2S2/c16-10-4-1-3-9(7-10)15(5-2-6-15)19-14-18-11-8-12(17)23-13(11)24(21,22)20-14/h1,3-4,7-8H,2,5-6H2,(H2,18,19,20)

Standard InChI Key:  DSCJXNXUTREXCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -0.3041   -0.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -0.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251   -1.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150   -0.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4486   -1.5767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353   -1.1701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353   -0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4486    0.0747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9471   -1.4226    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -1.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286   -0.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672   -2.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373   -2.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185    0.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2543   -0.7602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4128    0.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361    0.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1237    1.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5471   -0.3558    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 11  8  1  0
  5 14  2  0
 10  5  1  0
  5 15  2  0
  5  6  1  0
  7 16  1  0
  6  7  2  0
 13 17  1  0
 16  1  1  0
  7  8  1  0
  1 18  1  0
 10 11  2  0
 18 19  2  0
  4  1  1  0
 19 20  1  0
 20 21  2  0
  1  2  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 23 18  1  0
  3  4  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA383992

   ---

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: 402.33

Molecular Weight (Monoisotopic): 400.9826

AlogP: 4.19

#Rotatable Bonds: 2

Polar Surface Area: 70.56

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: 1.23

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -1.10

References

1. Nielsen FE, Ebdrup S, Jensen AF, Ynddal L, Bodvarsdottir TB, Stidsen C, Worsaae A, Boonen HC, Arkhammar PO, Fremming T, Wahl P, Kornø HT, Hansen JB..  (2006)  New 3-alkylamino-4H-thieno-1,2,4-thiadiazine 1,1-dioxide derivatives activate ATP-sensitive potassium channels of pancreatic beta cells.,  49  (14): [PMID:16821773] [10.1021/jm060042j]

Source

Source(1):

• Scientific Literature