(4S,6S)-4-(5-amino-2,3-difluorophenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-amine

ID: ALA3804964

PubChem CID: 127048531

Max Phase: Preclinical

Molecular Formula: C16H18F2N4OS

Molecular Weight: 352.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1noc(C)c1[C@@H]1C[C@@](C)(c2cc(N)cc(F)c2F)N=C(N)S1

Standard InChI:  InChI=1S/C16H18F2N4OS/c1-7-13(8(2)23-22-7)12-6-16(3,21-15(20)24-12)10-4-9(19)5-11(17)14(10)18/h4-5,12H,6,19H2,1-3H3,(H2,20,21)/t12-,16-/m0/s1

Standard InChI Key:  MENYBZSCSAVYMM-LRDDRELGSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3238    0.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -5.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464   -5.2884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2122   -3.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149   -3.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533   -3.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518   -3.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2643    2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520    2.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    4.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938    5.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    4.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5453    3.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403    5.0245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769    2.3253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350    5.1343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  2  7  1  0
  4  8  1  6
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9 13  1  0
 13 14  1  0
 11 15  1  0
  6 12  1  6
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 18 22  1  0
 17 23  1  0
 20 24  1  0
  4 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3804964

   ---

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: 352.41

Molecular Weight (Monoisotopic): 352.1169

AlogP: 3.56

#Rotatable Bonds: 2

Polar Surface Area: 90.43

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.13

CX LogP: 2.32

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: -0.83

References

1. Wu YJ, Guernon J, Yang F, Snyder L, Shi J, Mcclure A, Rajamani R, Park H, Ng A, Lewis H, Chang C, Camac D, Toyn JH, Ahlijanian MK, Albright CF, Macor JE, Thompson LA..  (2016)  Targeting the BACE1 Active Site Flap Leads to a Potent Inhibitor That Elicits Robust Brain Aβ Reduction in Rodents.,  7  (3): [PMID:26985314] [10.1021/acsmedchemlett.5b00432]

Source

Source(1):

• Scientific Literature