(E)-3-((1R,4R)-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-1-phenylprop-2-en-1-one

ID: ALA5191655

PubChem CID: 163408823

Max Phase: Preclinical

Molecular Formula: C20H19FN2O

Molecular Weight: 322.38

Names and Identifiers

Canonical SMILES:  O=C(/C=C/N1C[C@H]2C[C@@H]1CN2c1ccc(F)cc1)c1ccccc1

Standard InChI:  InChI=1S/C20H19FN2O/c21-16-6-8-17(9-7-16)23-14-18-12-19(23)13-22(18)11-10-20(24)15-4-2-1-3-5-15/h1-11,18-19H,12-14H2/b11-10+/t18-,19-/m1/s1

Standard InChI Key:  CSSHXOCDFOBNLZ-MMKWGKFASA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.0122    1.2021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    0.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -0.6188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002    0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847   -0.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    1.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847   -1.8563    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  4  3  1  0
  4  5  1  1
  6  4  1  0
  7  6  1  0
  2  7  1  0
  8  6  1  0
  9  8  2  0
 10  9  1  0
 10 11  2  0
 12 10  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
  4 18  1  0
 18 19  1  0
 19  2  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  2  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5191655

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 322.38

Molecular Weight (Monoisotopic): 322.1481

AlogP: 3.49

#Rotatable Bonds: 4

Polar Surface Area: 23.55

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.04

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: -0.57

References

1. He Y, Yang C, Wang Y, Sacher JR, Sims MM, Pfeffer LM, Miller DD..  (2022)  Novel structural-related analogs of PFI-3 (SRAPs) that target the BRG1 catalytic subunit of the SWI/SNF complex increase the activity of temozolomide in glioblastoma cells.,  53  [PMID:34863065] [10.1016/j.bmc.2021.116533]

Source

Source(1):

• Scientific Literature