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

ID: ALA3347583

PubChem CID: 118718052

Max Phase: Preclinical

Molecular Formula: C18H24BrNO2S

Molecular Weight: 398.37

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)N1S(C)(=O)=O

Standard InChI:  InChI=1S/C18H24BrNO2S/c1-11(2)9-14-17-16-12(7-6-8-13(16)19)15(10-18(17,3)4)20(14)23(5,21)22/h6-8,14-15,17H,1,9-10H2,2-5H3/t14-,15-,17-/m0/s1

Standard InChI Key:  CPSMRACROQFVFP-ZOBUZTSGSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.2367  -11.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4484  -12.0350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0284  -12.6104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -8.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3239   -9.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7405   -8.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2201  -10.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0508  -11.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0804   -9.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3624  -10.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1576  -10.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4783  -11.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6288  -10.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475  -10.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3195  -10.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1720  -11.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7545  -11.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8840  -10.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018  -10.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3281  -10.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5891  -11.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2124  -11.8015    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0792   -9.8039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1947   -9.2991    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.0327  -12.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  0
  6  5  1  0
 12  7  1  0
  7  8  1  0
  7  9  1  0
 13 10  1  0
  8 11  1  0
  9  5  1  0
 10 11  1  0
 10  5  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 11 18  1  6
 18 19  1  0
 19 20  2  0
 19 21  1  0
  7 22  1  1
 10 23  1  6
  8  2  1  0
 14 24  1  0
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347583

   ---

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: 398.37

Molecular Weight (Monoisotopic): 397.0711

AlogP: 4.61

#Rotatable Bonds: 3

Polar Surface Area: 37.38

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: 0.33

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