3-(2-Chloro-5-methoxy-phenyl)-3-fluoro-2-oxo-2,3-dihydro-1H-indole-7-carbonitrile

ID: ALA8069

PubChem CID: 44265000

Max Phase: Preclinical

Molecular Formula: C16H10ClFN2O2

Molecular Weight: 316.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cl)c(C2(F)C(=O)Nc3c(C#N)cccc32)c1

Standard InChI:  InChI=1S/C16H10ClFN2O2/c1-22-10-5-6-13(17)12(7-10)16(18)11-4-2-3-9(8-19)14(11)20-15(16)21/h2-7H,1H3,(H,20,21)

Standard InChI Key:  YVQQRDMMEJVMGI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.5750   -3.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -2.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -2.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -3.8625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -5.1625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875   -5.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  6  2  0
  8  9  3  0
  9  7  1  0
 10  5  1  0
 11  5  2  0
 12  2  2  0
  1 13  1  0
 14 10  2  0
 15  4  2  0
 16 11  1  0
 17 10  1  0
 18 16  2  0
 19 16  1  0
 20 21  2  0
 21 15  1  0
 22 19  1  0
  3  6  1  0
 18 14  1  0
  7 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA8069

   3-(2-chloro-5-methoxyphenyl)-3-fluoro-2-oxo-1H-indole-7-carbonitrile

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: 316.72

Molecular Weight (Monoisotopic): 316.0415

AlogP: 3.39

#Rotatable Bonds: 2

Polar Surface Area: 62.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.81

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.92

Np Likeness Score: -0.78

References

1. Hewawasam P, Gribkoff VK, Pendri Y, Dworetzky SI, Meanwell NA, Martinez E, Boissard CG, Post-Munson DJ, Trojnacki JT, Yeleswaram K, Pajor LM, Knipe J, Gao Q, Perrone R, Starrett JE..  (2002)  The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels.,  12  (7): [PMID:11909708] [10.1016/s0960-894x(02)00101-4]

Source

Source(1):

• Scientific Literature