(E)-1-(3,5-dibromo-2-hydroxyphenyl)-3-((1R,4R)-5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)prop-2-en-1-one

ID: ALA5189140

PubChem CID: 168278395

Max Phase: Preclinical

Molecular Formula: C19H18BrN3O2

Molecular Weight: 400.28

Names and Identifiers

Canonical SMILES:  O=C(/C=C/N1C[C@H]2C[C@@H]1CN2c1ccccn1)c1cccc(Br)c1O

Standard InChI:  InChI=1S/C19H18BrN3O2/c20-16-5-3-4-15(19(16)25)17(24)7-9-22-11-14-10-13(22)12-23(14)18-6-1-2-8-21-18/h1-9,13-14,25H,10-12H2/b9-7+/t13-,14-/m1/s1

Standard InChI Key:  ARBCURWIXUGNRF-BIYBCCJYSA-N

Molfile:  

 
     RDKit          2D

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    2.7267    1.2017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.6191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    0.6183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5700   -0.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5700    0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847    1.0305    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580   -1.4478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726   -0.2068    0.0000 C   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
 17 18  1  0
 16 19  1  0
  4 20  1  0
 20 21  1  0
 21  2  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5189140

   ---

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: 400.28

Molecular Weight (Monoisotopic): 399.0582

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 56.67

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.05

CX Basic pKa: 5.42

CX LogP: 3.58

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -0.39

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