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

ID: ALA3347502

PubChem CID: 118718001

Max Phase: Preclinical

Molecular Formula: C17H24BrN

Molecular Weight: 322.29

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H24BrN/c1-10(2)8-13-16-15-11(6-5-7-12(15)18)14(19-13)9-17(16,3)4/h5-7,10,13-14,16,19H,8-9H2,1-4H3/t13-,14-,16-/m0/s1

Standard InChI Key:  NVFMZIRQCMFQLH-DZKIICNBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   23.1500   -2.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5716   -3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9847   -2.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4686   -4.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2924   -5.3528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3301   -3.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6097   -4.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3983   -4.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7331   -5.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8824   -4.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3059   -4.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5840   -4.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4377   -5.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0153   -5.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4540   -3.3422    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.1186   -4.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8304   -4.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5506   -4.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8178   -5.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4610   -5.8255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.3205   -3.8447    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  1  0
 17 19  1  0
  4 20  1  1
  7 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3347502

   ---

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: 322.29

Molecular Weight (Monoisotopic): 321.1092

AlogP: 5.02

#Rotatable Bonds: 2

Polar Surface Area: 12.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.21

CX LogP: 4.99

CX LogD: 3.20

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.81

Np Likeness Score: 0.72

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