(S)-8,9-Dimethoxy-4-methyl-2,3,4,5,6,10b-hexahydro-1H-pyrrolo[2,1-a]isoquinolin-4-ium iodide

ID: ALA4081330

PubChem CID: 137647637

Max Phase: Preclinical

Molecular Formula: C15H22INO2

Molecular Weight: 248.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@@H]1CCC[N+]1(C)CC2.[I-]

Standard InChI:  InChI=1S/C15H22NO2.HI/c1-16-7-4-5-13(16)12-10-15(18-3)14(17-2)9-11(12)6-8-16;/h9-10,13H,4-8H2,1-3H3;1H/q+1;/p-1/t13-,16?;/m0./s1

Standard InChI Key:  DYXDGMZLSAHNNL-MRTSDAHRSA-M

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   32.4326  -10.0339    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   36.1669  -11.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1650  -10.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4502  -11.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4543  -10.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0247  -11.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7376  -11.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0288  -10.4114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7427  -10.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5783   -9.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7626   -9.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4232   -9.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4569   -9.5869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.3098  -10.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8822  -10.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8825  -11.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5976   -9.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6000  -11.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6025  -12.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3148  -10.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2 16  2  0
 15  3  2  0
  3  5  1  0
  4  5  2  0
  4  7  1  0
  5  9  1  0
  8  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  9 13  1  6
  8 14  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 17 20  1  0
M  CHG  2   1  -1   8   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: 248.35

Molecular Weight (Monoisotopic): 248.1645

AlogP: 2.54

#Rotatable Bonds: 2

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: -2.06

CX LogD: -2.06

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.75

Np Likeness Score: 1.33

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