5-Bromo-3-[2-(4-fluoro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one

ID: ALA127798

Cas Number: 601487-96-1

PubChem CID: 6918711

Max Phase: Preclinical

Molecular Formula: C16H9BrFNO2

Molecular Weight: 346.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccc(Br)cc2/C1=C\C(=O)c1ccc(F)cc1

Standard InChI:  InChI=1S/C16H9BrFNO2/c17-10-3-6-14-12(7-10)13(16(21)19-14)8-15(20)9-1-4-11(18)5-2-9/h1-8H,(H,19,21)/b13-8+

Standard InChI Key:  VVBIXEJMWRHSLL-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.6417   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -2.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -3.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -0.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.4250    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -1.4917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  1  1  0
  6  5  2  0
  7  4  1  0
  8  5  1  0
  9  2  2  0
 10  7  1  0
 11  7  2  0
 12  6  1  0
 13 10  2  0
 14 10  1  0
 15  8  2  0
 16 18  1  0
 17 15  1  0
 18 14  2  0
 19 13  1  0
 20 15  1  0
 21 16  1  0
  3  6  1  0
 12 17  2  0
 19 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA127798

   (3E)-5-bromo-3-[2-(4-fluorophenyl)-2-oxoethylidene]-1H-indol-2-one

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: 346.16

Molecular Weight (Monoisotopic): 344.9801

AlogP: 3.81

#Rotatable Bonds: 2

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.21

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.66

Np Likeness Score: -0.90

References

1. Woodard CL, Li Z, Kathcart AK, Terrell J, Gerena L, Lopez-Sanchez M, Kyle DE, Bhattacharjee AK, Nichols DA, Ellis W, Prigge ST, Geyer JA, Waters NC..  (2003)  Oxindole-based compounds are selective inhibitors of Plasmodium falciparum cyclin dependent protein kinases.,  46  (18): [PMID:12930149] [10.1021/jm0300983]

2. Bhattacharjee AK, Geyer JA, Woodard CL, Kathcart AK, Nichols DA, Prigge ST, Li Z, Mott BT, Waters NC..  (2004)  A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.,  47  (22): [PMID:15481979] [10.1021/jm040108f]

3. Cabrera DG, Horatscheck A, Wilson CR, Basarab G, Eyermann CJ, Chibale K..  (2018)  Plasmodial Kinase Inhibitors: License to Cure?,  61  (18): [PMID:29771541] [10.1021/acs.jmedchem.8b00329]

Source

Source(1):

• Scientific Literature