US9447085, 5

ID: ALA3938461

PubChem CID: 76284385

Max Phase: Preclinical

Molecular Formula: C19H23FN6O4S

Molecular Weight: 450.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/N=C(/Nc1ccc(F)c([C@]2(C)CS(=O)(=O)N(C)C(=N)N2)c1)c1ccc(OC)cn1

Standard InChI:  InChI=1S/C19H23FN6O4S/c1-19(11-31(27,28)26(2)18(21)24-19)14-9-12(5-7-15(14)20)23-17(25-30-4)16-8-6-13(29-3)10-22-16/h5-10H,11H2,1-4H3,(H2,21,24)(H,23,25)/t19-/m0/s1

Standard InChI Key:  VQGLZCUJHDZRDR-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
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   -0.0048   -2.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902   -3.7623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819   -5.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1752   -6.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638   -7.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8591   -8.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -9.4630    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5658   -7.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -6.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603   -8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -7.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5531   -8.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401  -10.4633    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5013  -11.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703   -9.8480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346  -11.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241  -12.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579  -10.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1023  -11.0316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -8.9407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3101   -0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3215    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6262    1.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6406    2.9977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6852    3.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9195    0.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081   -0.7629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
 11 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 13  1  0
  4 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  2  0
 31 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3938461

   N'-[3-[(5R)-3-amino-2,5-dimethyl-1,1-dioxo-6H-1,2,4-thiadiazin-5-yl]-4-fluorophenyl]-N,5-dimethoxypyridine-2-carboximidamide

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: 450.50

Molecular Weight (Monoisotopic): 450.1486

AlogP: 1.66

#Rotatable Bonds: 5

Polar Surface Area: 129.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.37

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -1.09

References

1.  (2016)  Iminothiadiazine dioxides containing a thioamide, amidine, or amide oxime group as BACE inhibitors, compositions, and their use, 

Source

Source(1):

• BindingDB Database