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

ID: ALA4440849

PubChem CID: 135126469

Max Phase: Preclinical

Molecular Formula: C20H19F2N5O3S

Molecular Weight: 447.47

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H19F2N5O3S/c1-4-7-30-18-11-24-17(10-25-18)16(22)9-13-5-6-15(21)14(8-13)20(2)12-31(28,29)27(3)19(23)26-20/h1,5-6,8-11H,7,12H2,2-3H3,(H2,23,26)/b16-9-/t20-/m0/s1

Standard InChI Key:  WIQPRGHWWVQNAA-CPYXBQISSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   31.5003  -13.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2089  -14.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9187  -13.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9161  -12.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1977  -12.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4908  -12.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6258  -12.3634    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.1940  -11.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9068  -11.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4889  -10.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4890  -11.1483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8981  -11.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9054  -10.3262    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.1970   -9.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6713  -10.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6080  -10.7308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7807   -9.9203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1960   -9.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7940  -14.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0849  -13.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3786  -14.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0821  -12.7866    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.6728  -13.6063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9670  -14.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9694  -14.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6834  -15.2407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3863  -14.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2636  -15.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2675  -16.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5617  -16.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8610  -16.8899    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
 14 18  1  0
  1 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4440849

   ---

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: 447.47

Molecular Weight (Monoisotopic): 447.1177

AlogP: 1.90

#Rotatable Bonds: 5

Polar Surface Area: 110.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.66

CX LogP: 1.47

CX LogD: 1.47

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.70

Np Likeness Score: -0.98

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