(R,S)2-[4-(Bis(4-fluorophenyl)methyl)piperazin-1-yl]-4-hydroxybutanamide

ID: ALA1651898

PubChem CID: 51031488

Max Phase: Preclinical

Molecular Formula: C21H25F2N3O2

Molecular Weight: 389.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)C(CCO)N1CCN(C(c2ccc(F)cc2)c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C21H25F2N3O2/c22-17-5-1-15(2-6-17)20(16-3-7-18(23)8-4-16)26-12-10-25(11-13-26)19(9-14-27)21(24)28/h1-8,19-20,27H,9-14H2,(H2,24,28)

Standard InChI Key:  BFBWMDDWOUKCDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   21.8841   -2.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721   -1.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6483   -1.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2364   -2.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721   -3.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7121   -2.3122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6483   -3.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8841   -0.8866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721   -0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8841    0.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7121    0.5390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1240   -0.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7121   -0.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1240    1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7121    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8841    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721    2.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8841    3.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7121    3.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1240    2.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721    4.1127    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.9479    1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3598    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1837    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5956    1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1837    0.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3598    0.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4194    1.2539    0.0000 F   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
 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
 14 15  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
 25 28  1  0
 14 22  1  0
 11 14  1  0
  2  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1651898

   2-[4-[Bis(4-fluorophenyl)methyl]piperazin-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: 389.45

Molecular Weight (Monoisotopic): 389.1915

AlogP: 1.91

#Rotatable Bonds: 7

Polar Surface Area: 69.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.43

CX LogP: 2.08

CX LogD: 2.04

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -0.69

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