trans-(4aR,8aR)-N-cyclohexyl-4a,5,6,7,8,8a-hexahydro-4,1,2-benzoxathiazin-3-amine 1,1-dioxide

ID: ALA2409732

PubChem CID: 136219291

Max Phase: Preclinical

Molecular Formula: C13H22N2O3S

Molecular Weight: 286.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)N=C(NC2CCCCC2)O[C@@H]2CCCC[C@H]21

Standard InChI:  InChI=1S/C13H22N2O3S/c16-19(17)12-9-5-4-8-11(12)18-13(15-19)14-10-6-2-1-3-7-10/h10-12H,1-9H2,(H,14,15)/t11-,12-/m1/s1

Standard InChI Key:  ZMDVQNCMHSXAPA-VXGBXAGGSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.0798   -5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798   -6.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947   -6.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -6.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947   -4.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2282   -6.5314    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -6.1197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2282   -4.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6619   -4.8798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3766   -5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3766   -6.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0914   -6.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8061   -6.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8061   -5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0914   -4.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -6.9475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -4.4680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -7.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -7.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
  4 18  1  1
  5 19  1  6
  7 20  2  0
 21  7  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409732

   ---

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: 286.40

Molecular Weight (Monoisotopic): 286.1351

AlogP: 1.94

#Rotatable Bonds: 1

Polar Surface Area: 67.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.80

Np Likeness Score: -0.26

References

1. Böhme T, Engel CK, Farjot G, Güssregen S, Haack T, Tschank G, Ritter K..  (2013)  1,1-Dioxo-5,6-dihydro-[4,1,2]oxathiazines, a novel class of 11ß-HSD1 inhibitors for the treatment of diabetes.,  23  (16): [PMID:23845218] [10.1016/j.bmcl.2013.05.102]

Source

Source(1):

• Scientific Literature