(4-((2-((Bis(4-fluorophenyl)methyl)sulfinyl)ethyl)amino)piperidin-1-yl)(phenyl)methanone

ID: ALA4757505

PubChem CID: 142590712

Max Phase: Preclinical

Molecular Formula: C27H28F2N2O2S

Molecular Weight: 482.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccccc1)N1CCC(NCC[S+]([O-])C(c2ccc(F)cc2)c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C27H28F2N2O2S/c28-23-10-6-20(7-11-23)26(21-8-12-24(29)13-9-21)34(33)19-16-30-25-14-17-31(18-15-25)27(32)22-4-2-1-3-5-22/h1-13,25-26,30H,14-19H2

Standard InChI Key:  CEHLZWQQNGVVIG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.5822   -1.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5811   -2.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988   -2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -1.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7071   -3.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1226   -3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296   -2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380   -3.0834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001   -4.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010   -5.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2438   -1.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9508   -1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6592   -1.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3662   -1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6605   -2.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0746   -1.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4129   -1.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3650   -0.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0719   -2.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7794   -3.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4874   -2.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4835   -1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7754   -1.4439    0.0000 C   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
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  1 18  1  0
 15 19  1  0
 12 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 21 26  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 25 27  1  0
  9 28  1  0
 25 29  2  0
 27 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 27  1  0
M  CHG  2   9   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4757505

   ---

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: 482.60

Molecular Weight (Monoisotopic): 482.1840

AlogP: 4.70

#Rotatable Bonds: 8

Polar Surface Area: 55.40

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.49

CX LogP: 3.59

CX LogD: 1.52

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.47

Np Likeness Score: -0.87

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