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

ID: ALA366809

PubChem CID: 44383751

Max Phase: Preclinical

Molecular Formula: C22H26N2O2

Molecular Weight: 350.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]([C@@H](O)c1ccc2c(c1)CC(=O)N2)N1CCC(c2ccccc2)CC1

Standard InChI:  InChI=1S/C22H26N2O2/c1-15(22(26)18-7-8-20-19(13-18)14-21(25)23-20)24-11-9-17(10-12-24)16-5-3-2-4-6-16/h2-8,13,15,17,22,26H,9-12,14H2,1H3,(H,23,25)/t15-,22+/m0/s1

Standard InChI Key:  HJRGLUUTXXPQKZ-OYHNWAKOSA-N

Molfile:  

     RDKit          2D

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   -0.1083   -3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -2.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -2.4792    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  2  1  0
 12  2  1  0
 13  3  2  0
 14 15  2  0
 15  5  1  0
 16 18  1  0
 17 11  1  0
 18 12  1  0
 19 16  1  0
  8 20  1  6
  7 21  1  1
 22 19  2  0
 23 19  1  0
 24 23  2  0
 25 22  1  0
 26 24  1  0
  4 10  1  0
  9  6  2  0
 17 16  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA366809

   5-[(1S,2S)-1-Hydroxy-2-(4-phenyl-piperidin-1-yl)-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: 350.46

Molecular Weight (Monoisotopic): 350.1994

AlogP: 3.48

#Rotatable Bonds: 4

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: 9.16

CX LogP: 3.07

CX LogD: 1.31

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.89

Np Likeness Score: -0.36

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