N-{1-[2-(4-Isothiocyanato-phenyl)-ethyl]-piperidin-4-yl}-N-phenyl-propionamide

ID: ALA274844

Cas Number: 85951-63-9

PubChem CID: 84008

Max Phase: Preclinical

Molecular Formula: C23H27N3OS

Molecular Weight: 393.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N(c1ccccc1)C1CCN(CCc2ccc(N=C=S)cc2)CC1

Standard InChI:  InChI=1S/C23H27N3OS/c1-2-23(27)26(21-6-4-3-5-7-21)22-13-16-25(17-14-22)15-12-19-8-10-20(11-9-19)24-18-28/h3-11,22H,2,12-17H2,1H3

Standard InChI Key:  VDKBIFPJULZUPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.4254   -3.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544    4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254   -0.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399    3.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    4.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9965   -3.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399    2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254   -0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399    0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254    2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544    2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254    1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544    1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9965   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  1  0
  4 13  1  0
  5  1  1  0
  6 14  1  0
  7  2  2  0
  8  5  1  0
  9  5  1  0
 10  3  2  0
 11  1  1  0
 12  8  1  0
 13  9  1  0
 14 19  1  0
 15  4  1  0
 16 17  1  0
 17 15  1  0
 18 20  1  0
 19 21  2  0
 20 16  2  0
 21 16  1  0
 22  3  1  0
 23 11  2  0
 24 11  1  0
 25 22  1  0
 26 23  1  0
 27 24  2  0
 28 27  1  0
 12  4  1  0
 26 28  2  0
 18 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA274844

   Fentanyl isothiocyanate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 393.56

Molecular Weight (Monoisotopic): 393.1875

AlogP: 4.87

#Rotatable Bonds: 7

Polar Surface Area: 35.91

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 4.84

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.37

References

1. Burke TR, Jacobson AE, Rice KC, Silverton JV, Simonds WF, Streaty RA, Klee WA..  (1986)  Probes for narcotic receptor mediated phenomena. 12. cis-(+)-3-Methylfentanyl isothiocyanate, a potent site-directed acylating agent for delta opioid receptors. Synthesis, absolute configuration, and receptor enantioselectivity.,  29  (6): [PMID:3012085] [10.1021/jm00156a030]

2. Burke TR, Bajwa BS, Jacobson AE, Rice KC, Streaty RA, Klee WA..  (1984)  Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for mu or delta opiate receptors.,  27  (12): [PMID:6150112] [10.1021/jm00378a008]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays