9-Benzyloxy-8-methoxy-4-methyl-2,3,4,5,6,10b-hexahydro-1H-pyrrolo[2,1-a]isoquinolin-4-ium iodide

ID: ALA4087153

PubChem CID: 137642935

Max Phase: Preclinical

Molecular Formula: C20H24INO2

Molecular Weight: 310.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1Oc1ccccc1)C1CCC[N+]1(C)CC2.[I-]

Standard InChI:  InChI=1S/C20H24NO2.HI/c1-21-11-6-9-18(21)17-14-20(23-16-7-4-3-5-8-16)19(22-2)13-15(17)10-12-21;/h3-5,7-8,13-14,18H,6,9-12H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  BVIIBRRPGACIEL-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   20.0377  -28.1147    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   20.9413  -30.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6551  -29.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6522  -29.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9395  -28.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2291  -29.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2332  -29.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8124  -29.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5210  -30.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8165  -29.1067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5260  -28.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3635  -27.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5535  -27.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2140  -28.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3675  -30.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3688  -31.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3625  -28.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3595  -27.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0674  -27.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0646  -26.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3507  -26.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6422  -26.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6485  -27.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1020  -29.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  6  9  1  0
  7 11  1  0
 10  8  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  3 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 10 24  1  0
M  CHG  2   1  -1  10   1
M  END

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: 310.42

Molecular Weight (Monoisotopic): 310.1802

AlogP: 4.33

#Rotatable Bonds: 3

Polar Surface Area: 18.46

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: 0.90

References

1. Crestey F, Jensen AA, Soerensen C, Magnus CB, Andreasen JT, Peters GHJ, Kristensen JL..  (2018)  Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.,  61  (4): [PMID:29384668] [10.1021/acs.jmedchem.7b01895]

Source

Source(1):

• Scientific Literature