5-{2-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-1-hydroxy-ethyl}-1,3-dihydro-indol-2-one

ID: ALA173092

PubChem CID: 14580202

Max Phase: Preclinical

Molecular Formula: C22H25FN2O2

Molecular Weight: 368.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Cc2cc(C(O)CN3CCC(Cc4ccc(F)cc4)CC3)ccc2N1

Standard InChI:  InChI=1S/C22H25FN2O2/c23-19-4-1-15(2-5-19)11-16-7-9-25(10-8-16)14-21(26)17-3-6-20-18(12-17)13-22(27)24-20/h1-6,12,16,21,26H,7-11,13-14H2,(H,24,27)

Standard InChI Key:  JZAYUGIZPPLLGT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -0.0208   -4.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -4.1792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  2  0
  4  1  1  0
  5  9  1  0
  6  3  1  0
  7 13  1  0
  8  2  1  0
  9 10  1  0
 10  7  1  0
 11  2  2  0
 12  4  1  0
 13 12  2  0
 14  5  1  0
 15  5  1  0
 16 18  1  0
 17 22  1  0
 18 21  1  0
 19 10  1  0
 20 17  1  0
 21 27  1  0
 22 25  2  0
 23 24  1  0
 24 16  2  0
 25 16  1  0
 26 14  1  0
 27 15  1  0
  3  8  1  0
  6  7  2  0
 26 21  1  0
 23 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA173092

   5-{2-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-1-hydroxy-ethyl}-1,3-dihydro-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: 368.45

Molecular Weight (Monoisotopic): 368.1900

AlogP: 3.31

#Rotatable Bonds: 5

Polar Surface Area: 52.57

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.18

CX Basic pKa: 8.83

CX LogP: 3.24

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -0.90

References

1. Chenard B, Butler T, Shalaby I, Prochniak M, Koe B, Fox C.  (1993)  Oxindole N-Methyl-D-Aspartate (NMDA) antagonists,  3  (1): [10.1016/S0960-894X(00)80098-0]

Source

Source(1):

• Scientific Literature