(1R,8S,10S)-3,6-Dibromo-11,11-dimethyl-10-(2-methyl-allyl)-9-aza-tricyclo[6.2.2.0(2,7)]dodeca-2(7),3,5-triene

ID: ALA3347492

PubChem CID: 1014304

Max Phase: Preclinical

Molecular Formula: C17H21Br2N

Molecular Weight: 399.17

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)ccc(Br)c12

Standard InChI:  InChI=1S/C17H21Br2N/c1-9(2)7-12-16-15-11(19)6-5-10(18)14(15)13(20-12)8-17(16,3)4/h5-6,12-13,16,20H,1,7-8H2,2-4H3/t12-,13-,16-/m0/s1

Standard InChI Key:  LQZVTORZIAYQLZ-XEZPLFJOSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.2913   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7165   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1331   -3.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6127   -5.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4434   -5.7241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4730   -4.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7550   -4.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5502   -4.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8709   -5.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0214   -4.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4401   -4.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7121   -4.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5646   -5.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1471   -5.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5895   -3.6966    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.2766   -4.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9944   -5.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7207   -4.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9817   -5.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6050   -6.2009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4717   -4.2033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0025   -6.7213    0.0000 Br  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
 14 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347492

   (1R,8S,10S)-3,6-dibromo-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: 399.17

Molecular Weight (Monoisotopic): 397.0041

AlogP: 5.70

#Rotatable Bonds: 2

Polar Surface Area: 12.03

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.19

CX LogP: 5.41

CX LogD: 4.57

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.63

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