{3-[6-Fluoro-1-(2-fluoro-phenyl)-2,2-dioxo-1,2,3,4-tetrahydro-2lambda*6*-benzo[c][1,2]thiazin-3-yl]-propyl}-methyl-amine

ID: ALA1096001

PubChem CID: 25109441

Max Phase: Preclinical

Molecular Formula: C18H20F2N2O2S

Molecular Weight: 366.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCCC1Cc2cc(F)ccc2N(c2ccccc2F)S1(=O)=O

Standard InChI:  InChI=1S/C18H20F2N2O2S/c1-21-10-4-5-15-12-13-11-14(19)8-9-17(13)22(25(15,23)24)18-7-3-2-6-16(18)20/h2-3,6-9,11,15,21H,4-5,10,12H2,1H3

Standard InChI Key:  CLLQMGVKRYVVFS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.6962    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    0.5000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    0.5000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    7.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    2.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641    4.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9641    3.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    3.5000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0
  2  3  2  0
  2  6  1  0
  3  7  1  0
  4  5  1  0
  4 10  1  0
  5 15  1  0
  6 16  2  0
  7 18  2  0
  8  9  1  0
  8 14  2  0
  9 17  2  0
 10 21  1  0
 11 13  2  0
 11 14  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 14 19  1  0
 15 25  1  0
 16 18  1  0
 16 20  1  0
 17 22  1  0
 18 22  1  0
 22 25  1  0
 23 25  2  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096001

   3-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxido-3,4-dihydro-1H-2,1-benzothiazin-3-yl]-N-methylpropan-1-amine

2. Alternative Forms:

   

   ALA1096001

   3-[6-fluoro-1-(2-fluorophenyl)-2,2-dioxo-3,4-dihydro-2lambda6,1-benzothiazin-3-yl]-N-methylpropan-1-amine;hydrochloride

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: 366.43

Molecular Weight (Monoisotopic): 366.1214

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 49.41

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.24

CX LogP: 3.13

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.89

References

1. Fensome A, Goldberg J, McComas CC, Trybulski EJ, Woodworth RP, Deecher DC, Whiteside GT, Zhang P..  (2010)  Structure-activity relationships of norepinephrine reuptake inhibitors with benzothiadiazine dioxide or dihydrosulfostyril cores.,  20  (5): [PMID:20153188] [10.1016/j.bmcl.2010.01.056]

Source

Source(1):

• Scientific Literature