(+/-)-(1S,4R,9S)-5-Bromo-3,3-dimethyl-9-(2-methylallyl)-10-pentyl-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalene

ID: ALA3347550

PubChem CID: 118718026

Max Phase: Preclinical

Molecular Formula: C22H32BrN

Molecular Weight: 390.41

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)N1CCCCC

Standard InChI:  InChI=1S/C22H32BrN/c1-6-7-8-12-24-18(13-15(2)3)21-20-16(10-9-11-17(20)23)19(24)14-22(21,4)5/h9-11,18-19,21H,2,6-8,12-14H2,1,3-5H3/t18-,19-,21-/m0/s1

Standard InChI Key:  OPJZVCVVRSRNPP-ZJOUEHCJSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   16.8763  -10.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3012   -9.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1886  -11.7761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5881  -11.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0351  -11.2947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1429  -10.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7218   -8.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6009  -10.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7168  -11.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1964  -10.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3342  -10.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1287  -11.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5994  -10.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0638   -9.7593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1612   -9.2497    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.0168  -12.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2776  -10.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8720   -8.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0126  -10.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4475  -11.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4384  -12.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0554   -9.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7703  -13.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3401  -10.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1919  -12.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9531  -13.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  3  1  1
 19 17  2  0
 19 15  1  0
  8  4  1  0
 25 23  1  0
  8 11  2  0
 21 16  1  0
 17 12  1  0
 24  6  1  0
  9 20  1  0
 20 13  2  0
 24 14  1  6
  5 21  1  0
  7  2  1  0
 22  2  1  0
  2 18  1  0
 10  5  1  0
 13 24  1  0
 10 22  1  0
  5  6  1  0
 12  9  2  0
 16 25  1  0
  6  1  1  6
 24  2  1  0
 13 19  1  0
  1  8  1  0
 20 10  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347550

   ---

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: 390.41

Molecular Weight (Monoisotopic): 389.1718

AlogP: 6.84

#Rotatable Bonds: 6

Polar Surface Area: 3.24

Molecular Species: BASE

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.18

CX LogP: 6.80

CX LogD: 5.02

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: 0.41

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