US9181236, 78

ID: ALA3964648

PubChem CID: 71532491

Max Phase: Preclinical

Molecular Formula: C21H18ClF3N2O2S2

Molecular Weight: 486.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(c2sc(C#CCc3cc(F)c(F)c(F)c3)cc2Cl)CS(=O)(=O)C2(CCC2)C(=N)N1

Standard InChI:  InChI=1S/C21H18ClF3N2O2S2/c1-20(11-31(28,29)21(6-3-7-21)19(26)27-20)18-14(22)10-13(30-18)5-2-4-12-8-15(23)17(25)16(24)9-12/h8-10H,3-4,6-7,11H2,1H3,(H2,26,27)/t20-/m0/s1

Standard InChI Key:  GBJQQTZKCKUYBI-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 31 34  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
   -0.7535    1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    1.2961    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603    1.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347    2.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0691   -1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0691    1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606   -1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590   -2.3362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535   -1.2961    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
    2.1876    1.4714    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4653    2.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    2.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224    2.8509    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8195    3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761    4.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5326    4.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7675    4.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1242    4.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3567    3.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4420    4.3146    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.2325    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2185    1.6238    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8758    1.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7765    0.4721    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6433    2.5229    0.0000 C   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  7  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13  2  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  2  0
 18 19  1  0
 16 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 31 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3964648

   (7S)-7-[3-chloro-5-[3-(3,4,5-trifluorophenyl)prop-1-ynyl]thiophen-2-yl]-7-methyl-5,5-dioxo-5lambda6-thia-8-azaspiro[3.5]non-8-en-9-amine

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: 486.97

Molecular Weight (Monoisotopic): 486.0450

AlogP: 4.55

#Rotatable Bonds: 2

Polar Surface Area: 70.02

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.32

CX LogP: 5.00

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.51

References

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

Source

Source(1):

• BindingDB Database