US9242943, 37

ID: ALA3954950

PubChem CID: 57520409

Max Phase: Preclinical

Molecular Formula: C21H22N4O2

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cnc2c(Nc3cccc(C4(C)COCC(N)=N4)c3)cccc2c1

Standard InChI:  InChI=1S/C21H22N4O2/c1-21(13-27-12-19(22)25-21)15-6-4-7-16(10-15)24-18-8-3-5-14-9-17(26-2)11-23-20(14)18/h3-11,24H,12-13H2,1-2H3,(H2,22,25)

Standard InChI Key:  IGUZINVHWNCBIH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   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 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
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5054    5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1985    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7972    2.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7906    1.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7680    4.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0705    5.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3661    4.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3592    2.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0568    2.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3957    2.3481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -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
    0.0000   -1.5000    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  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 20 22  1  0
  7 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26  6  1  0
 26 27  2  0
 27  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3954950

   5-[3-[(3-Methoxyquinolin-8-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-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: 3.59

#Rotatable Bonds: 4

Polar Surface Area: 81.76

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: 2.42

CX LogD: 1.27

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -0.48

References

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

Source

Source(1):

• BindingDB Database