(R)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one

ID: ALA8347

Cas Number: 187523-36-0

PubChem CID: 656757

Max Phase: Preclinical

Molecular Formula: C16H10ClF4NO2

Molecular Weight: 359.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cl)cc1[C@@]1(F)C(=O)Nc2cc(C(F)(F)F)ccc21

Standard InChI:  InChI=1S/C16H10ClF4NO2/c1-24-13-5-3-9(17)7-11(13)15(18)10-4-2-8(16(19,20)21)6-12(10)22-14(15)23/h2-7H,1H3,(H,22,23)/t15-/m1/s1

Standard InChI Key:  ULYONBAOIMCNEH-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
    4.4042   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -4.2125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -2.1292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.6542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -2.8125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -5.4667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -5.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -6.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  6
  4  2  1  0
  5  1  1  0
  6  5  1  0
  7  8  1  0
  8 14  2  0
  9  6  2  0
 10  5  2  0
 11  3  1  0
 12  3  2  0
 13  2  2  0
 14 10  1  0
  1 15  1  1
 16  7  1  0
 17  7  1  0
 18  7  1  0
 19 11  2  0
 20 12  1  0
 21 20  2  0
 22 20  1  0
 23 11  1  0
 24 23  1  0
  4  6  1  0
  9  8  1  0
 21 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA8347

   (3R)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-6-(trifluoromethyl)indolin-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: 359.71

Molecular Weight (Monoisotopic): 359.0336

AlogP: 4.53

#Rotatable Bonds: 2

Polar Surface Area: 38.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.56

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.65

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