(R,S)N-Benzyl-4-hydroxy-2-(piperazin-1-yl)butanamide

ID: ALA1651899

PubChem CID: 51031624

Max Phase: Preclinical

Molecular Formula: C15H23N3O2

Molecular Weight: 277.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)C(CCO)N1CCNCC1

Standard InChI:  InChI=1S/C15H23N3O2/c19-11-6-14(18-9-7-16-8-10-18)15(20)17-12-13-4-2-1-3-5-13/h1-5,14,16,19H,6-12H2,(H,17,20)

Standard InChI Key:  UOQZXGVRRGDKLP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    0.6275   -7.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842   -8.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275   -8.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -7.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275   -6.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001   -7.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -7.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -6.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001   -6.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -8.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -5.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275   -4.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -4.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -4.8333    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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 12  1  0
  2  7  1  0
  4 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
  6 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1651899

   N-benzyl-4-hydroxy-2-piperazin-1-ylbutanamide

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: 277.37

Molecular Weight (Monoisotopic): 277.1790

AlogP: -0.04

#Rotatable Bonds: 6

Polar Surface Area: 64.60

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.92

CX LogP: -0.14

CX LogD: -1.66

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.68

Np Likeness Score: -0.73

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