N-{1-[2-(4-Isothiocyanato-phenyl)-ethyl]-3-methyl-piperidin-4-yl}-N-phenyl-propionamide

ID: ALA273222

PubChem CID: 14099644

Max Phase: Preclinical

Molecular Formula: C24H29N3OS

Molecular Weight: 407.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N(c1ccccc1)[C@@H]1CCN(CCc2ccc(N=C=S)cc2)C[C@H]1C

Standard InChI:  InChI=1S/C24H29N3OS/c1-3-24(28)27(22-7-5-4-6-8-22)23-14-16-26(17-19(23)2)15-13-20-9-11-21(12-10-20)25-18-29/h4-12,19,23H,3,13-17H2,1-2H3/t19-,23-/m1/s1

Standard InChI Key:  ZQESQBVNDBLWAM-AUSIDOKSSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  1  0  0  0  0  0999 V2000
    6.7667   -0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -0.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -1.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937    0.1381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292    1.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0792    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  9  2  0
  5  1  1  0
  6  2  1  0
  7 13  1  0
  8  3  1  0
  9 14  1  0
 10  4  2  0
 11  1  1  0
 12  5  2  0
 13  6  1  0
 14 19  1  0
 15  7  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
  3 22  1  1
 23  5  1  0
 24 11  2  0
 25 11  1  0
 26 23  1  0
 27 24  1  0
 28 25  2  0
 29 28  1  0
  8  7  1  0
 27 29  2  0
 18 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA273222

   N-[(3R,4R)-1-[2-(4-isothiocyanatophenyl)ethyl]-3-methylpiperidin-4-yl]-N-phenylpropanamide

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: 407.58

Molecular Weight (Monoisotopic): 407.2031

AlogP: 5.12

#Rotatable Bonds: 7

Polar Surface Area: 35.91

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.83

CX LogP: 5.32

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -0.91

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. Kim CH, Rothman RB, Jacobson AE, Mattson MV, Bykov V, Streaty RA, Klee WA, George C, Long JB, Rice KC..  (1989)  Probes for narcotic receptor mediated phenomena. 15. (3S,4S)-(+)-trans-3-methylfentanyl isothiocyanate, a potent site-directed acylating agent for the delta opioid receptors in vitro.,  32  (6): [PMID:2542560] [10.1021/jm00126a040]

Source

Source(1):

• Scientific Literature