(R,S)N-Benzyl-2-(4-benzylpiperidin-1-yl)-4-hydroxybutanamide

ID: ALA1651903

PubChem CID: 51031628

Max Phase: Preclinical

Molecular Formula: C23H30N2O2

Molecular Weight: 366.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)C(CCO)N1CCC(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C23H30N2O2/c26-16-13-22(23(27)24-18-21-9-5-2-6-10-21)25-14-11-20(12-15-25)17-19-7-3-1-4-8-19/h1-10,20,22,26H,11-18H2,(H,24,27)

Standard InChI Key:  QBXQUHDWRHHXNO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.0583  -13.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6458  -13.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0583  -14.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8833  -14.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8833  -13.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6458  -12.3619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2958  -13.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8208  -13.7894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4083  -14.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833  -14.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708  -13.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833  -13.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4083  -13.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3458  -13.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9333  -13.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083  -13.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9333  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0583  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8833  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2958  -10.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1208  -10.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5333  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1208  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2958  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  4  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 11 14  1  0
  2  8  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
  6 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1651903

   N-benzyl-2-(4-benzylpiperidin-1-yl)-4-hydroxybutanamide

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: 366.51

Molecular Weight (Monoisotopic): 366.2307

AlogP: 3.01

#Rotatable Bonds: 8

Polar Surface Area: 52.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.01

CX LogP: 3.11

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.55

References

1. Kulig K, Więckowski K, Więckowska A, Gajda J, Pochwat B, Höfner GC, Wanner KT, Malawska B..  (2011)  Synthesis and biological evaluation of new derivatives of 2-substituted 4-hydroxybutanamides as GABA uptake inhibitors.,  46  (1): [PMID:21111516] [10.1016/j.ejmech.2010.11.001]

Source

Source(1):

• Scientific Literature