4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)butyl 4-carbamoylbenzoate

ID: ALA5198792

PubChem CID: 168286423

Max Phase: Preclinical

Molecular Formula: C23H27ClN2O4

Molecular Weight: 430.93

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc(C(=O)OCCCCN2CCC(O)(c3ccc(Cl)cc3)CC2)cc1

Standard InChI:  InChI=1S/C23H27ClN2O4/c24-20-9-7-19(8-10-20)23(29)11-14-26(15-12-23)13-1-2-16-30-22(28)18-5-3-17(4-6-18)21(25)27/h3-10,29H,1-2,11-16H2,(H2,25,27)

Standard InChI Key:  VVWAEFSEWWHXPN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.0162    2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8023    3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0077    3.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    2.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6351    2.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4303    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3859    3.8694    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0516    1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6711    1.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8846    0.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2652    0.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8380    2.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -0.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794   -0.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8765   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600   -0.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570   -0.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -1.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4706    0.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378   -1.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2190   -1.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0053   -2.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -2.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261   -2.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -3.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -2.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752   -3.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  2  7  1  0
  5  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
  8 13  1  0
  8 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 23 21  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 21 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5198792

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 430.93

Molecular Weight (Monoisotopic): 430.1659

AlogP: 3.36

#Rotatable Bonds: 8

Polar Surface Area: 92.86

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 9.00

CX LogP: 2.99

CX LogD: 1.39

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -0.68

References

1. Dichiara M, Artacho-Cordón A, Turnaturi R, Santos-Caballero M, González-Cano R, Pasquinucci L, Barbaraci C, Rodríguez-Gómez I, Gómez-Guzmán M, Marrazzo A, Cobos EJ, Amata E..  (2022)  Dual Sigma-1 receptor antagonists and hydrogen sulfide-releasing compounds for pain treatment: Design, synthesis, and pharmacological evaluation.,  230  [PMID:35016113] [10.1016/j.ejmech.2021.114091]

Source

Source(1):

• Scientific Literature