N-(2-((Bis(4-fluorophenyl)methyl)sulfinyl)ethyl)-1-neopentylpiperidin-4-amine

ID: ALA4764168

PubChem CID: 142590741

Max Phase: Preclinical

Molecular Formula: C25H34F2N2OS

Molecular Weight: 448.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)CN1CCC(NCC[S+]([O-])C(c2ccc(F)cc2)c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C25H34F2N2OS/c1-25(2,3)18-29-15-12-23(13-16-29)28-14-17-31(30)24(19-4-8-21(26)9-5-19)20-6-10-22(27)11-7-20/h4-11,23-24,28H,12-18H2,1-3H3

Standard InChI Key:  VXPYZLOZKBNJQW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.2492  -17.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2480  -18.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9561  -18.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6657  -18.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6629  -17.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9543  -16.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3741  -18.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3754  -19.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0812  -18.1347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.7895  -18.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4966  -18.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2049  -18.5399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6670  -19.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6679  -20.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3768  -20.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0862  -20.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0818  -19.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5414  -16.9094    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.3792  -21.8116    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.9120  -18.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.9107  -17.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6178  -16.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3261  -17.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0332  -16.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3274  -18.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7415  -17.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7428  -18.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4486  -16.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4461  -17.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0736  -17.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  8 13  2  0
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  1 18  1  0
 15 19  1  0
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 20 21  1  0
 20 22  1  0
 22 23  1  0
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 24 25  1  0
 24 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  9 31  1  0
M  CHG  2   9   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4764168

   ---

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: 448.62

Molecular Weight (Monoisotopic): 448.2360

AlogP: 4.90

#Rotatable Bonds: 8

Polar Surface Area: 38.33

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.53

CX LogP: 4.13

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.79

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