[2H]-(1R,3S,4S,5R)-3-[[4-amino-3-fluoro-5-[(1R)-2,2,2-trifluoro-1-(methoxymethyl)ethoxy]phenyl]methyl]-5-[[(3-tert-butylphenyl)-dideuterio-methyl]amino]-1-oxido-tetrahydrothiopyran-1-ium-4-ol

ID: ALA2425617

PubChem CID: 72191343

Max Phase: Preclinical

Molecular Formula: C27H36F4N2O4S

Molecular Weight: 560.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [2H]C([2H])(N[C@H]1C[S@+]([O-])C[C@@H](Cc2cc(F)c(N)c(O[C@H](COC)C(F)(F)F)c2)[C@@H]1O)c1cccc(C(C)(C)C)c1

Standard InChI:  InChI=1S/C27H36F4N2O4S/c1-26(2,3)19-7-5-6-16(9-19)12-33-21-15-38(35)14-18(25(21)34)8-17-10-20(28)24(32)22(11-17)37-23(13-36-4)27(29,30)31/h5-7,9-11,18,21,23,25,33-34H,8,12-15,32H2,1-4H3/t18-,21+,23-,25+,38-/m1/s1/i12D2

Standard InChI Key:  FIUDDEQHPBHZBI-CPTQHNDESA-N

Molfile:  

     RDKit          2D

 40 42  0  0  0  0  0  0  0  0999 V2000
   13.2292  -11.9959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6459  -12.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0582  -11.9933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5042  -11.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7958  -11.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7958  -12.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5078  -13.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2199  -12.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2199  -11.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5078  -13.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9337  -13.1261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0819  -13.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3669  -12.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3687  -11.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6545  -11.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9397  -11.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9435  -12.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6583  -13.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2311  -13.1381    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240  -11.4823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6537  -10.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5023  -10.6459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9389  -10.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9380   -9.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2248  -10.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098  -10.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958  -10.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6521   -9.0042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2232   -9.0056    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9333   -8.5916    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3627  -13.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3585  -13.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0716  -14.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7877  -13.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7861  -13.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0726  -12.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4998  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2152  -13.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4981  -11.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2084  -12.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  6  1  0
  5  4  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  7 10  1  1
  8 11  1  6
  6 12  1  6
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
 16 20  1  0
 15 21  1  0
  4 22  1  1
 21 23  1  0
 23 24  1  0
 23 25  1  6
 25 26  1  0
 26 27  1  0
 24 28  1  0
 24 29  1  0
 24 30  1  0
 11  2  1  0
  2 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 37 40  1  0
M  CHG  2   4   1  22  -1
M  ISO  2   1   2   3   2
M  END

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: 560.65

Molecular Weight (Monoisotopic): 560.2332

AlogP: 4.10

#Rotatable Bonds: 9

Polar Surface Area: 99.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.25

CX LogP: 3.30

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -0.26

References

1. Rueeger H, Lueoend R, Machauer R, Veenstra SJ, Jacobson LH, Staufenbiel M, Desrayaud S, Rondeau JM, Möbitz H, Neumann U..  (2013)  Discovery of cyclic sulfoxide hydroxyethylamines as potent and selective β-site APP-cleaving enzyme 1 (BACE1) inhibitors: structure based design and in vivo reduction of amyloid β-peptides.,  23  (19): [PMID:23981898] [10.1016/j.bmcl.2013.07.071]

Source

Source(1):

• Scientific Literature