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

ID: ALA3347549

PubChem CID: 118718025

Max Phase: Preclinical

Molecular Formula: C24H27BrFN

Molecular Weight: 428.39

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)N1Cc1cccc(F)c1

Standard InChI:  InChI=1S/C24H27BrFN/c1-15(2)11-20-23-22-18(9-6-10-19(22)25)21(13-24(23,3)4)27(20)14-16-7-5-8-17(26)12-16/h5-10,12,20-21,23H,1,11,13-14H2,2-4H3/t20-,21-,23-/m0/s1

Standard InChI Key:  FTMDWWFQMQJEKJ-FUDKSRODSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.9065   -7.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316   -8.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7483   -7.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279  -10.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0585  -10.6727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0882   -9.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702   -9.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -9.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860  -10.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366   -9.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0553   -9.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273   -9.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797  -10.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622  -10.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -9.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -9.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3359   -9.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5969  -10.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2202  -11.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -9.1518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581  -11.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405  -12.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258  -12.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082  -12.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078  -13.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -13.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4430  -12.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4312  -14.2084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2025   -8.6470    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
  8 15  1  6
 15 16  1  0
 16 17  2  0
 16 18  1  0
  4 19  1  1
  7 20  1  6
  5 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 11 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347549

   ---

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: 428.39

Molecular Weight (Monoisotopic): 427.1311

AlogP: 6.99

#Rotatable Bonds: 4

Polar Surface Area: 3.24

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.79

CX LogP: 6.90

CX LogD: 6.36

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -0.23

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