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

ID: ALA4777080

PubChem CID: 142590720

Max Phase: Preclinical

Molecular Formula: C27H27F3N2O2S

Molecular Weight: 500.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(F)cc1)N1CCC(NCC[S+]([O-])C(c2ccc(F)cc2)c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C27H27F3N2O2S/c28-22-7-1-19(2-8-22)26(20-3-9-23(29)10-4-20)35(34)18-15-31-25-13-16-32(17-14-25)27(33)21-5-11-24(30)12-6-21/h1-12,25-26,31H,13-18H2

Standard InChI Key:  ASMWBPNCBDZFBV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.9468   -2.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6548   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3645   -2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3616   -1.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1953   -2.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9036   -3.0834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3657   -4.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3667   -5.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.0248   -1.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7319   -1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7786   -1.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7306   -0.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4376   -2.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1411   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5620   -3.0756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
  4  5  1  0
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  8 13  2  0
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  1 18  1  0
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 20 21  1  0
 20 22  1  0
 22 23  1  0
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 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
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 32 35  1  0
M  CHG  2   9   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4777080

   ---

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: 500.59

Molecular Weight (Monoisotopic): 500.1745

AlogP: 4.84

#Rotatable Bonds: 8

Polar Surface Area: 55.40

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.49

CX LogP: 3.73

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.45

Np Likeness Score: -0.82

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