1-(Thiophen-2-yl)-4-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)butane-1,4-dione

ID: ALA4794136

PubChem CID: 71523423

Max Phase: Preclinical

Molecular Formula: C19H19F3N2O2S

Molecular Weight: 396.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCC(=O)N1CCN(c2ccc(C(F)(F)F)cc2)CC1)c1cccs1

Standard InChI:  InChI=1S/C19H19F3N2O2S/c20-19(21,22)14-3-5-15(6-4-14)23-9-11-24(12-10-23)18(26)8-7-16(25)17-2-1-13-27-17/h1-6,13H,7-12H2

Standard InChI Key:  RGFTZQFKSFKLOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.5766  -21.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627  -21.5653    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8619  -21.1603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663  -21.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794  -21.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941  -21.1671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856  -20.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663  -20.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3155  -21.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7208  -21.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421  -21.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9516  -22.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7729  -22.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2486  -23.2692    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0311  -23.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0348  -22.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2546  -21.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435  -21.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6320  -20.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114  -20.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014  -21.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139  -21.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331  -21.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670  -20.4481    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273  -20.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5404  -23.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
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  8  9  1  0
  7 10  1  0
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 15 16  1  0
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 17 18  1  0
 18 14  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 24 19  1  0
  4 19  1  0
 22  2  1  0
  2 25  1  0
 10 26  2  0
 13 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794136

   1-Thiophen-2-yl-4-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]butane-1,4-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.43

Molecular Weight (Monoisotopic): 396.1119

AlogP: 4.08

#Rotatable Bonds: 5

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.86

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.97

References

1. Devine R,Kelada M,Leonard S,Martin DSD,Walsh JMD,Breen CJ,Driver RB,Kinsella GK,Findlay JBC,Stephens JC.  (2020)  Design, synthesis, and biological evaluation of aryl piperazines with potential as antidiabetic agents via the stimulation of glucose uptake and inhibition of NADH:ubiquinone oxidoreductase.,  202  [PMID:32645646] [10.1016/j.ejmech.2020.112416]

Source

Source(1):

• Scientific Literature