2-methyl-1'-phenethyl-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidin]-1-one

ID: ALA5284021

Max Phase: Preclinical

Molecular Formula: C22H26N2O

Molecular Weight: 334.46

Names and Identifiers

Canonical SMILES:  CN1CC2(CCN(CCc3ccccc3)CC2)c2ccccc2C1=O

Standard InChI:  InChI=1S/C22H26N2O/c1-23-17-22(20-10-6-5-9-19(20)21(23)25)12-15-24(16-13-22)14-11-18-7-3-2-4-8-18/h2-10H,11-17H2,1H3

Standard InChI Key:  KJXSXVBYEBIWOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.7852    2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    3.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586    2.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586    1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    1.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    2.6807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    3.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.2073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3586    1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705   -1.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705   -2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -2.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -3.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695   -3.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -3.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -2.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    3.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    3.9185    0.0000 O   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
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 10  1  0
  7 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
  7 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
  9 24  1  0
 10 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284021

   ---

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: 334.46

Molecular Weight (Monoisotopic): 334.2045

AlogP: 3.35

#Rotatable Bonds: 3

Polar Surface Area: 23.55

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.22

CX LogP: 3.31

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.28

References

1. Zhuang T, Xiong J, Hao S, Du W, Liu Z, Liu B, Zhang G, Chen Y..  (2021)  Bifunctional μ opioid and σ₁ receptor ligands as novel analgesics with reduced side effects.,  223  [PMID:34175542] [10.1016/j.ejmech.2021.113658]

Source

Source(1):

• Scientific Literature