US9181236, Table A, 16

ID: ALA3915097

PubChem CID: 89419819

Max Phase: Preclinical

Molecular Formula: C15H18FN3O4S

Molecular Weight: 355.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(c2cc([N+](=O)[O-])ccc2F)CS(=O)(=O)C2(CCCC2)C(=N)N1

Standard InChI:  InChI=1S/C15H18FN3O4S/c1-14(11-8-10(19(20)21)4-5-12(11)16)9-24(22,23)15(13(17)18-14)6-2-3-7-15/h4-5,8H,2-3,6-7,9H2,1H3,(H2,17,18)/t14-/m0/s1

Standard InChI Key:  AMKVFRZWMZCNRI-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
    0.5756   -1.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540    1.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621    1.2970    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618    1.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6362    2.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909    1.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236   -0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909   -1.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2621   -1.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606   -2.3371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -1.2970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    1.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2100    1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9297    2.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1497    3.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    3.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0695    2.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692    2.5527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.6882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042    3.7419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0558    1.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
 17 22  1  0
 22 23  2  0
 22 24  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3915097

   US9181236, Table A, 16

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: 355.39

Molecular Weight (Monoisotopic): 355.1002

AlogP: 2.26

#Rotatable Bonds: 2

Polar Surface Area: 113.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.50

CX LogP: 1.89

CX LogD: 1.53

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: -0.93

References

1.  (2015)  2-spiro-substituted iminothiazines and their mono-and dioxides as bace inhibitors, compositions and their use, 

Source

Source(1):

• BindingDB Database