(+/-)-(1S,4R,9S)-5-Bromo-3,3-dimethyl-9-(2-methylallyl)-10-(quinolin-4-ylmethyl)-1,2,3,4-tetra-hydro-1,4-(epiminomethano)naphthalene

ID: ALA3347524

PubChem CID: 118718011

Max Phase: Preclinical

Molecular Formula: C27H29BrN2

Molecular Weight: 461.45

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)N1Cc1ccnc2ccccc12

Standard InChI:  InChI=1S/C27H29BrN2/c1-17(2)14-23-26-25-20(9-7-10-21(25)28)24(15-27(26,3)4)30(23)16-18-12-13-29-22-11-6-5-8-19(18)22/h5-13,23-24,26H,1,14-16H2,2-4H3/t23-,24-,26-/m0/s1

Standard InChI Key:  KDFQIICGIIYXMB-GNKBHMEESA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   10.7041   -8.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1292   -9.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5458   -8.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0254  -10.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8561  -11.0771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8857   -9.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1677   -9.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9629  -10.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2836  -11.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4341  -10.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8528   -9.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1248  -10.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9773  -10.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5598  -11.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6893   -9.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4071  -10.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1334   -9.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3944  -11.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0177  -11.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8845   -9.5563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2556  -11.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -12.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0233  -12.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6058  -13.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054  -13.8936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0000   -9.0515    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.2406  -13.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8276  -13.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2268  -14.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0389  -14.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4501  -13.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0485  -13.2045    0.0000 C   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 28  1  0
 27 22  1  0
 11 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347524

   ---

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: 461.45

Molecular Weight (Monoisotopic): 460.1514

AlogP: 7.40

#Rotatable Bonds: 4

Polar Surface Area: 16.13

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.49

CX LogP: 6.91

CX LogD: 5.79

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: 0.05

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