1-(2-((Bis(4-fluorophenyl)methyl)thio)ethyl)-N-(4-(trifluoromethyl)benzyl)piperidin-4-amine

ID: ALA4784884

PubChem CID: 142590699

Max Phase: Preclinical

Molecular Formula: C28H29F5N2S

Molecular Weight: 520.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Fc1ccc(C(SCCN2CCC(NCc3ccc(C(F)(F)F)cc3)CC2)c2ccc(F)cc2)cc1

Standard InChI:  InChI=1S/C28H29F5N2S/c29-24-9-3-21(4-10-24)27(22-5-11-25(30)12-6-22)36-18-17-35-15-13-26(14-16-35)34-19-20-1-7-23(8-2-20)28(31,32)33/h1-12,26-27,34H,13-19H2

Standard InChI Key:  CSTKTLLYTLGMSB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   18.4225   -9.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4214  -10.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1336  -10.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8473  -10.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8445   -9.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1318   -9.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5598  -10.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5611  -11.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2710  -10.2434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9835  -10.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6947  -10.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4072  -10.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8486  -11.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8495  -12.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5626  -13.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2761  -12.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2717  -11.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7147   -9.0140    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.5649  -13.9410    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.4047  -11.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1090  -11.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8226  -11.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8232  -10.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1103  -10.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5335  -11.8905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2462  -11.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9572  -11.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9504  -12.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6605  -13.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3742  -12.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3734  -11.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6627  -11.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0857  -13.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0849  -13.9506    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.7937  -12.7172    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.7903  -13.5373    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
  1 18  1  0
 15 19  1  0
 12 20  1  0
 12 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4784884

   ---

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: 520.61

Molecular Weight (Monoisotopic): 520.1972

AlogP: 7.06

#Rotatable Bonds: 9

Polar Surface Area: 15.27

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.41

CX LogP: 6.82

CX LogD: 4.70

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: -1.14

References

1. Giancola JB,Bonifazi A,Cao J,Ku T,Haraczy AJ,Lam J,Rais R,Coggiano MA,Tanda G,Newman AH.  (2020)  Structure-activity relationships for a series of (Bis(4-fluorophenyl)methyl)sulfinylethyl-aminopiperidines and -piperidine amines at the dopamine transporter: Bioisosteric replacement of the piperazine improves metabolic stability.,  208  [PMID:32947229] [10.1016/j.ejmech.2020.112674]

Source

Source(1):

• Scientific Literature