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

ID: ALA4077524

PubChem CID: 137650261

Max Phase: Preclinical

Molecular Formula: C14H18INO2

Molecular Weight: 232.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[N+]12CCC[C@H]1c1cc3c(cc1CC2)OCO3.[I-]

Standard InChI:  InChI=1S/C14H18NO2.HI/c1-15-5-2-3-12(15)11-8-14-13(16-9-17-14)7-10(11)4-6-15;/h7-8,12H,2-6,9H2,1H3;1H/q+1;/p-1/t12-,15?;/m0./s1

Standard InChI Key:  WTWBYKLODFKUNB-VPCQFMPWSA-M

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   15.9927   -3.3506    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   19.7274   -4.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7256   -3.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0107   -4.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0148   -3.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5849   -4.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2980   -4.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5891   -3.7281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3031   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1386   -2.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3229   -2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9834   -3.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0174   -2.9036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8700   -4.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4428   -3.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4432   -4.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2313   -4.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7183   -4.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2309   -3.4708    0.0000 O   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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  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: 232.30

Molecular Weight (Monoisotopic): 232.1332

AlogP: 2.25

#Rotatable Bonds: ┄

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: -2.12

CX LogD: -2.12

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.64

Np Likeness Score: 1.56

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