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

ID: ALA3347584

PubChem CID: 118718053

Max Phase: Preclinical

Molecular Formula: C23H25BrFNO2S

Molecular Weight: 478.43

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(=O)(=O)c1ccc(F)cc1

Standard InChI:  InChI=1S/C23H25BrFNO2S/c1-14(2)12-19-22-21-17(6-5-7-18(21)24)20(13-23(22,3)4)26(19)29(27,28)16-10-8-15(25)9-11-16/h5-11,19-20,22H,1,12-13H2,2-4H3/t19-,20-,22-/m0/s1

Standard InChI Key:  GZMCRXQGKJRDGQ-ONTIZHBOSA-N

Molfile:  

     RDKit          2D

 31 34  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
    7.2166  -12.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8010  -13.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2038  -14.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0265  -14.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4385  -13.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897  -14.8510    0.0000 F   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
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347584

   ---

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: 478.43

Molecular Weight (Monoisotopic): 477.0773

AlogP: 6.18

#Rotatable Bonds: 4

Polar Surface Area: 37.38

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.01

CX LogD: 6.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.32

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