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

ID: ALA1651900

PubChem CID: 51031625

Max Phase: Preclinical

Molecular Formula: C15H22ClN3O2

Molecular Weight: 311.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Cl)cc1)C(CCO)N1CCNCC1

Standard InChI:  InChI=1S/C15H22ClN3O2/c16-13-3-1-12(2-4-13)11-18-15(21)14(5-10-20)19-8-6-17-7-9-19/h1-4,14,17,20H,5-11H2,(H,18,21)

Standard InChI Key:  KLUJDBKZZHZQHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    7.6566   -7.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -7.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -8.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566   -8.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -7.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566   -6.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291   -7.1937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -7.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015   -7.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015   -6.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -5.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291   -6.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -8.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -5.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -5.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566   -4.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566   -3.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -3.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0884   -3.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0884   -4.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3725   -2.6521    0.0000 Cl  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
 18 21  1  0
  6 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1651900

   N-[(4-chlorophenyl)methyl]-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: 311.81

Molecular Weight (Monoisotopic): 311.1401

AlogP: 0.61

#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: 8.91

CX LogP: 0.46

CX LogD: -1.06

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: -0.94

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