(+/-)-(1S,4R,9S)-3,3-Dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-epiminomethano)naphthalene

ID: ALA3347501

PubChem CID: 7233583

Max Phase: Preclinical

Molecular Formula: C17H23N

Molecular Weight: 241.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@@H]1N[C@H]2CC(C)(C)[C@@H]1c1ccccc12

Standard InChI:  InChI=1S/C17H23N/c1-11(2)9-14-16-13-8-6-5-7-12(13)15(18-14)10-17(16,3)4/h5-8,14-16,18H,1,9-10H2,2-4H3/t14-,15-,16+/m0/s1

Standard InChI Key:  ZVZCYSQBQLWXCC-HRCADAONSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   16.5317   -3.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9568   -3.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3735   -3.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8531   -5.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6837   -5.8851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7133   -4.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9954   -4.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7906   -5.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1112   -5.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2618   -5.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6805   -4.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9525   -4.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8049   -5.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3874   -6.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5169   -4.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2347   -5.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9611   -4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2221   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8454   -6.3618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7121   -4.3642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  9  4  1  0
  4  5  1  0
  4  6  1  0
 10  7  1  0
  5  8  1  0
  6  2  1  0
  7  8  1  0
  7  2  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  6
 15 16  1  0
 16 17  2  0
 16 18  1  0
  4 19  1  1
  7 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3347501

   (1R,8S,10S)-11,11-dimethyl-10-(2-methylprop-2-enyl)-9-azatricyclo[6.2.2.02,7]dodeca-2,4,6-triene

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: 241.38

Molecular Weight (Monoisotopic): 241.1830

AlogP: 4.18

#Rotatable Bonds: 2

Polar Surface Area: 12.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.23

CX LogP: 3.88

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.77

Np Likeness Score: 0.96

References

1. Cifuentes-Pagano E, Saha J, Csányi G, Ghouleh IA, Sahoo S, Rodríguez A, Wipf P, Pagano PJ, Skoda EM..  (2013)  Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox2) inhibitors.,  4  (7): [PMID:24466406] [10.1039/c3md00061c]

2.  (2014)  Tetrahydroisoquinolines as selective nadph oxidase 2 inhibitors, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data