US9242943, 46

ID: ALA3912220

PubChem CID: 57520310

Max Phase: Preclinical

Molecular Formula: C21H22N4O2

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(c2cccc(Nc3cccc4oc(C5CC5)nc34)c2)COCC(N)=N1

Standard InChI:  InChI=1S/C21H22N4O2/c1-21(12-26-11-18(22)25-21)14-4-2-5-15(10-14)23-16-6-3-7-17-19(16)24-20(27-17)13-8-9-13/h2-7,10,13,23H,8-9,11-12H2,1H3,(H2,22,25)

Standard InChI Key:  QPTMIQYCEQIDKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    4.1424    3.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1850    3.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4516    2.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7472    3.0012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7403    4.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    5.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1423    4.4894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4324    6.4453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1903    1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920    0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    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
   -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
   -2.4133   -1.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -2.9665    0.0000 N   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
   -2.5536   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386   -5.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778   -5.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 15  1  0
 23 19  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 24  1  0
 13 27  2  0
 27  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3912220

   N-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-2-cyclopropyl-1,3-benzoxazol-4-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: 362.43

Molecular Weight (Monoisotopic): 362.1743

AlogP: 4.05

#Rotatable Bonds: 4

Polar Surface Area: 85.67

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.54

CX LogP: 2.67

CX LogD: 1.52

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.54

References

1.  (2016)  1,4 oxazines as BACE1 and/or BACE2 inhibitors, 

Source

Source(1):

• BindingDB Database