5-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5,6-dihydro-4H-1,2,4-oxadiazine

ID: ALA4872778

PubChem CID: 124127337

Max Phase: Preclinical

Molecular Formula: C20H17F4N5O2

Molecular Weight: 435.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1nc(C2=NOCC(c3ccc(C(F)(F)F)c(F)c3)N2)ccc1-n1cnc(C)c1

Standard InChI:  InChI=1S/C20H17F4N5O2/c1-11-8-29(10-25-11)17-6-5-15(27-19(17)30-2)18-26-16(9-31-28-18)12-3-4-13(14(21)7-12)20(22,23)24/h3-8,10,16H,9H2,1-2H3,(H,26,28)

Standard InChI Key:  XHQUVJSIKVYGTC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.2137  -15.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125  -16.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206  -17.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303  -16.7460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274  -15.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9188  -15.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9204  -17.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280  -18.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045  -17.1545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609  -16.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136  -17.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217  -18.1398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211  -17.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010  -17.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336  -15.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441  -15.9225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7481  -15.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493  -14.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402  -14.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300  -14.6985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4558  -15.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4510  -16.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1579  -17.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8666  -16.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8640  -15.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1565  -15.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5702  -15.5085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5748  -17.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5759  -17.9658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.2820  -16.7391    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.2768  -17.5572    0.0000 F   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
  3  7  1  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 11 14  1  0
  5 15  1  0
 15 16  1  0
 15 20  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872778

   ---

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: 435.38

Molecular Weight (Monoisotopic): 435.1318

AlogP: 3.76

#Rotatable Bonds: 4

Polar Surface Area: 73.56

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.83

CX LogP: 3.68

CX LogD: 3.67

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -0.84

References

1. Bursavich MG, Harrison BA, Acharya R, Costa DE, Freeman EA, Hrdlicka LA, Jin H, Kapadnis S, Moffit JS, Murphy D, Nolan SJ, Patzke H, Tang C, Van Voorhies HE, Wen M, Koenig G, Blain JF, Burnett DA..  (2021)  Discovery of the Oxadiazine FRM-024: A Potent CNS-Penetrant Gamma Secretase Modulator.,  64  (19.0): [PMID:34550687] [10.1021/acs.jmedchem.1c00904]

Source

Source(1):

• Scientific Literature