8-methoxy-9-phenoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline

ID: ALA4067398

PubChem CID: 137633236

Max Phase: Preclinical

Molecular Formula: C19H21NO2

Molecular Weight: 295.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1Oc1ccccc1)C1CCCN1CC2

Standard InChI:  InChI=1S/C19H21NO2/c1-21-18-12-14-9-11-20-10-5-8-17(20)16(14)13-19(18)22-15-6-3-2-4-7-15/h2-4,6-7,12-13,17H,5,8-11H2,1H3

Standard InChI Key:  ZNGIYFCATPLRNY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   25.4606  -23.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1744  -23.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1716  -22.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4588  -22.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7484  -23.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7525  -22.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3359  -23.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0444  -23.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3399  -22.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0494  -22.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8828  -21.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0728  -21.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7374  -22.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8869  -23.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8881  -24.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8819  -22.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8788  -21.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5908  -21.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5881  -20.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8742  -19.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1616  -20.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1678  -21.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  2 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067398

   ---

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: 295.38

Molecular Weight (Monoisotopic): 295.1572

AlogP: 4.18

#Rotatable Bonds: 3

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.03

CX LogP: 3.76

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: 0.13

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