5-[(1S,2S)-2-(4-Benzyl-piperidin-1-yl)-1-hydroxy-propyl]-1,3-dihydro-indol-2-one

ID: ALA427116

PubChem CID: 9929020

Max Phase: Preclinical

Molecular Formula: C23H28N2O2

Molecular Weight: 364.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]([C@@H](O)c1ccc2c(c1)CC(=O)N2)N1CCC(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C23H28N2O2/c1-16(23(27)19-7-8-21-20(14-19)15-22(26)24-21)25-11-9-18(10-12-25)13-17-5-3-2-4-6-17/h2-8,14,16,18,23,27H,9-13,15H2,1H3,(H,24,26)/t16-,23+/m0/s1

Standard InChI Key:  FCXXSNGUDWIOQU-QMHKHESXSA-N

Molfile:  

     RDKit          2D

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    2.9125   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -3.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  1  1  0
  4  5  2  0
  5  1  1  0
  6 14  1  0
  7  8  1  0
  8  6  1  0
  9  4  1  0
 10  3  1  0
 11  3  2  0
 12  2  1  0
 13  2  1  0
 14 15  2  0
 15  5  1  0
  8 16  1  6
 17 20  1  0
 18 12  1  0
 19 13  1  0
 20 19  1  0
 21 17  1  0
  7 22  1  1
 23 21  2  0
 24 21  1  0
 25 24  2  0
 26 23  1  0
 27 25  1  0
  4 10  1  0
  9  6  2  0
 18 20  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA427116

   5-[(1S,2S)-2-(4-Benzyl-piperidin-1-yl)-1-hydroxy-propyl]-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: 364.49

Molecular Weight (Monoisotopic): 364.2151

AlogP: 3.56

#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: 9.11

CX LogP: 3.52

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -0.27

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