1-(4-((2-((Bis(4-fluorophenyl)methyl)sulfinyl)ethyl)amino)piperidin-1-yl)-2,2-dimethylpropan-1-one

ID: ALA4756427

PubChem CID: 142590756

Max Phase: Preclinical

Molecular Formula: C25H32F2N2O2S

Molecular Weight: 462.61

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H32F2N2O2S/c1-25(2,3)24(30)29-15-12-22(13-16-29)28-14-17-32(31)23(18-4-8-20(26)9-5-18)19-6-10-21(27)11-7-19/h4-11,22-23,28H,12-17H2,1-3H3

Standard InChI Key:  VFHIMUADSQZYDC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    2.7556  -17.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544  -18.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625  -19.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721  -18.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693  -17.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607  -17.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805  -19.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8818  -20.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5876  -18.7826    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2959  -19.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0030  -18.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7113  -19.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734  -20.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1743  -21.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832  -21.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926  -21.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882  -20.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0478  -17.5574    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8856  -22.4596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.4184  -18.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1267  -19.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4171  -17.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1242  -17.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325  -17.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5396  -17.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8338  -18.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2479  -17.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2492  -18.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9550  -17.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9525  -18.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800  -17.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5383  -16.7319    0.0000 O   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
 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
 27 28  1  0
 27 29  1  0
 27 30  1  0
  9 31  1  0
 25 32  2  0
M  CHG  2   9   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4756427

   ---

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: 462.61

Molecular Weight (Monoisotopic): 462.2153

AlogP: 4.43

#Rotatable Bonds: 7

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: 3.53

CX LogD: 1.47

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -0.90

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