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

ID: ALA1099373

PubChem CID: 46881677

Max Phase: Preclinical

Molecular Formula: C18H19F3N2O2S

Molecular Weight: 384.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCCC1Cc2cc(F)ccc2N(c2c(F)cccc2F)S1(=O)=O

Standard InChI:  InChI=1S/C18H19F3N2O2S/c1-22-9-3-4-14-11-12-10-13(19)7-8-17(12)23(26(14,24)25)18-15(20)5-2-6-16(18)21/h2,5-8,10,14,22H,3-4,9,11H2,1H3

Standard InChI Key:  KPUDPAXPYHVNAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.3660    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    6.5000    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
    3.9641    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    7.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    7.0000    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
    3.0981    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    6.5000    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
    2.2321    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    7.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    4.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    7.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    5.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    3.1340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    4.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0
  2  5  2  0
  2  6  1  0
  3  4  1  0
  3  9  1  0
  4 14  1  0
  5 15  1  0
  6 16  2  0
  7  8  1  0
  7 13  2  0
  8 17  2  0
  9 22  1  0
 10 12  2  0
 10 13  1  0
 11 12  1  0
 11 14  1  0
 12 17  1  0
 13 19  1  0
 14 26  1  0
 15 18  2  0
 15 20  1  0
 16 18  1  0
 16 21  1  0
 17 23  1  0
 18 23  1  0
 23 26  1  0
 24 26  2  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099373

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

2. Alternative Forms:

   

   ALA1099373

   3-[1-(2,6-difluorophenyl)-6-fluoro-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: 384.42

Molecular Weight (Monoisotopic): 384.1119

AlogP: 3.50

#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: 3.27

CX LogD: 0.58

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -0.79

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