5-(3-chloro-4-fluorophenyl)-3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5,6-dihydro-4H-1,2,4-oxadiazine

ID: ALA4878938

PubChem CID: 124127340

Max Phase: Preclinical

Molecular Formula: C19H17ClFN5O2

Molecular Weight: 401.83

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H17ClFN5O2/c1-11-8-26(10-22-11)17-6-5-15(24-19(17)27-2)18-23-16(9-28-25-18)12-3-4-14(21)13(20)7-12/h3-8,10,16H,9H2,1-2H3,(H,23,25)

Standard InChI Key:  CVLLIWGXQNSEIU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.0815  -15.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0803  -16.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7884  -16.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4980  -16.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4952  -15.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7866  -15.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7882  -17.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4958  -18.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3723  -16.8532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6287  -16.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0814  -17.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4895  -17.8385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2889  -17.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2688  -17.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2014  -15.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9118  -15.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6159  -15.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6170  -14.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9080  -13.9878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1977  -14.3972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3236  -15.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3188  -16.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0256  -16.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7343  -16.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7317  -15.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0243  -15.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4380  -15.2072    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.4426  -16.8474    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
M  END

Alternative Forms

1. Parent:

   

   ALA4878938

   ---

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: 401.83

Molecular Weight (Monoisotopic): 401.1055

AlogP: 3.40

#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: 3.41

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -1.12

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