Tilidine

ID: ALA4550731

Cas Number: 38690-93-6

PubChem CID: 12546498

Max Phase: Preclinical

Molecular Formula: C17H23NO2

Molecular Weight: 273.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@]1(c2ccccc2)CCC=C[C@@H]1N(C)C

Standard InChI:  InChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17+/m0/s1

Standard InChI Key:  WDEFBBTXULIOBB-DOTOQJQBSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   10.6978   -9.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6978  -10.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4031  -10.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -10.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083   -9.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4031   -9.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9913   -9.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9902   -8.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2821   -7.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5747   -8.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5797   -9.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2825   -9.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4031   -8.2297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1108   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6953   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1158  -10.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2986  -10.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4253  -10.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8865  -10.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0693  -10.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1  7  1  1
  6 13  1  1
 13 14  1  0
 13 15  1  0
  1 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550731

   Tilidine, (-)-

Molecule Features

Natural Product: Yes

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: 273.38

Molecular Weight (Monoisotopic): 273.1729

AlogP: 2.77

#Rotatable Bonds: 4

Polar Surface Area: 29.54

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.60

CX LogP: 3.35

CX LogD: 2.13

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 0.57

References

1. Meyer MJ, Neumann VE, Friesacher HR, Zdrazil B, Brockmöller J, Tzvetkov MV..  (2019)  Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.,  62  (21): [PMID:31597043] [10.1021/acs.jmedchem.9b01301]

Source

Source(1):

• Scientific Literature