6-chloro-3-(1-phenylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine1,1-dioxide

ID: ALA379292

PubChem CID: 135428234

Max Phase: Preclinical

Molecular Formula: C14H12ClN3O2S2

Molecular Weight: 353.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)NC(NC2(c3ccccc3)CC2)=Nc2cc(Cl)sc21

Standard InChI:  InChI=1S/C14H12ClN3O2S2/c15-11-8-10-12(21-11)22(19,20)18-13(16-10)17-14(6-7-14)9-4-2-1-3-5-9/h1-5,8H,6-7H2,(H2,16,17,18)

Standard InChI Key:  NSHQOOIHPDLZQY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    0.6171  -25.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387  -25.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0279  -24.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167  -25.6452    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035  -25.2385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035  -24.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167  -23.9936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154  -25.4911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8300  -25.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8300  -24.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6162  -24.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969  -24.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353  -26.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055  -26.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134  -23.9998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9228  -24.8285    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7449  -24.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561  -24.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683  -24.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712  -23.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559  -22.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424  -23.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  9  4  1  0
  4 13  2  0
  4  5  1  0
  4 14  2  0
  5  6  1  0
  6 15  1  0
  6  7  2  0
 12 16  1  0
 15  3  1  0
  9 10  2  0
  3 17  1  0
  1  3  1  0
 17 18  2  0
 18 19  1  0
  2  1  1  0
 19 20  2  0
  3  2  1  0
 20 21  1  0
 10  7  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA379292

   ---

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: 353.86

Molecular Weight (Monoisotopic): 353.0059

AlogP: 2.96

#Rotatable Bonds: 2

Polar Surface Area: 70.56

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.48

CX Basic pKa: 1.42

CX LogP: 3.36

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.87

Np Likeness Score: -0.96

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