(R)-5-{2-Fluoro-5-[2-fluoro-2-(5-prop-2-ynyloxy-pyrazin-2-yl)-vinyl]-phenyl}-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

ID: ALA4470897

PubChem CID: 135125856

Max Phase: Preclinical

Molecular Formula: C22H22F2N4O3S

Molecular Weight: 460.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#CCOc1cnc(/C(F)=C/c2ccc(F)c([C@]3(C)CS(=O)(=O)C(C)(C)C(N)=N3)c2)cn1

Standard InChI:  InChI=1S/C22H22F2N4O3S/c1-5-8-31-19-12-26-18(11-27-19)17(24)10-14-6-7-16(23)15(9-14)22(4)13-32(29,30)21(2,3)20(25)28-22/h1,6-7,9-12H,8,13H2,2-4H3,(H2,25,28)/b17-10-/t22-/m0/s1

Standard InChI Key:  MAJFETMMCMCMPJ-VBBNHBBTSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   39.2553  -13.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9640  -13.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6738  -13.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6711  -12.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9528  -12.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2459  -12.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3809  -12.1818    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.9491  -11.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6619  -10.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2440  -10.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2440  -10.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6532  -11.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6604  -10.1446    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.9520   -9.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4264   -9.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.3631  -10.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5358   -9.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5490  -13.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8399  -13.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1336  -13.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8371  -12.6050    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.4279  -13.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7221  -13.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7244  -14.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4385  -15.0591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1414  -14.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0187  -15.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0225  -15.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3168  -16.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6161  -16.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9511   -8.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2417   -9.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  8  5  1  1
  8  9  1  0
  8 11  1  0
 13  9  1  0
 14 10  1  0
 10 11  2  0
  8 12  1  0
 13 14  1  0
 13 15  2  0
 13 16  2  0
 10 17  1  0
  1 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  3  0
 14 31  1  0
 14 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4470897

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 460.51

Molecular Weight (Monoisotopic): 460.1381

AlogP: 2.87

#Rotatable Bonds: 5

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.71

CX LogP: 1.96

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.69

Np Likeness Score: -0.87

References

1. Hsiao CC, Rombouts F, Gijsen HJM..  (2019)  New evolutions in the BACE1 inhibitor field from 2014 to 2018.,  29  (6): [PMID:30709653] [10.1016/j.bmcl.2018.12.049]

Source

Source(1):

• Scientific Literature