(+/-)-(1S,4R,9S)-5-Bromo-3,3-dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-(epimino-methano)-naphthalene

ID: ALA3347491

PubChem CID: 1226613

Max Phase: Preclinical

Molecular Formula: C17H22BrN

Molecular Weight: 320.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@@H]1N[C@H]2CC(C)(C)[C@@H]1c1c(Br)cccc12

Standard InChI:  InChI=1S/C17H22BrN/c1-10(2)8-13-16-15-11(6-5-7-12(15)18)14(19-13)9-17(16,3)4/h5-7,13-14,16,19H,1,8-9H2,2-4H3/t13-,14-,16-/m0/s1

Standard InChI Key:  PNQKGQJZPWPRDM-DZKIICNBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    3.7043   -2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -3.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461   -2.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257   -5.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8563   -5.5838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859   -4.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1680   -4.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -5.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530   -4.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -4.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9775   -5.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -3.5563    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6895   -4.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4073   -4.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -4.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3946   -5.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0180   -6.0605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847   -4.0630    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
 11 15  1  0
  8 16  1  6
 16 17  1  0
 17 18  2  0
 17 19  1  0
  4 20  1  1
  7 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3347491

   (1R,8S,10S)-3-bromo-11,11-dimethyl-10-(2-methylprop-2-enyl)-9-azatricyclo[6.2.2.02,7]dodeca-2(7),3,5-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: 320.27

Molecular Weight (Monoisotopic): 319.0936

AlogP: 4.94

#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: 9.11

CX LogP: 4.65

CX LogD: 2.94

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.76

Np Likeness Score: 0.70

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