(+/-)-(1S,4R,9S)-10-((1H-Indol-3-yl)methyl)-5-bromo-3,3-dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalene

ID: ALA3347525

PubChem CID: 118718012

Max Phase: Preclinical

Molecular Formula: C26H29BrN2

Molecular Weight: 449.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@H]1[C@H]2c3c(Br)cccc3[C@H](CC2(C)C)N1Cc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C26H29BrN2/c1-16(2)12-22-25-24-19(9-7-10-20(24)27)23(13-26(25,3)4)29(22)15-17-14-28-21-11-6-5-8-18(17)21/h5-11,14,22-23,25,28H,1,12-13,15H2,2-4H3/t22-,23-,25-/m0/s1

Standard InChI Key:  FVPRTPRXRXZWDJ-LSQMVHIFSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   17.7121   -7.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1372   -8.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5539   -7.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0335  -10.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8641  -10.5860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8937   -9.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1758   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9710   -9.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2916  -10.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4422   -9.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8609   -9.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1328   -9.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9853  -10.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5678  -10.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6973   -9.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4151   -9.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1415   -9.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4024  -10.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0258  -11.0627    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8925   -9.0652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2637  -11.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8461  -12.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0081   -8.5603    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.0339  -12.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8538  -12.8771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1704  -12.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5565  -13.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7136  -14.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4841  -14.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0978  -13.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9375  -13.0158    0.0000 C   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
  5 21  1  0
 21 22  1  0
 11 23  1  0
 22 24  2  0
 24 25  1  0
 25 27  1  0
 26 22  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347525

   ---

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: 449.44

Molecular Weight (Monoisotopic): 448.1514

AlogP: 7.34

#Rotatable Bonds: 4

Polar Surface Area: 19.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.60

CX LogP: 6.85

CX LogD: 5.63

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 0.27

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