(+/-)-(1S,4R,9S)-10-(Benzo[d][1,3]dioxol-5-ylmethyl)-5-bromo-3,3-dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalene

ID: ALA3347542

PubChem CID: 118718020

Max Phase: Preclinical

Molecular Formula: C25H28BrNO2

Molecular Weight: 454.41

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)N1Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C25H28BrNO2/c1-15(2)10-19-24-23-17(6-5-7-18(23)26)20(12-25(24,3)4)27(19)13-16-8-9-21-22(11-16)29-14-28-21/h5-9,11,19-20,24H,1,10,12-14H2,2-4H3/t19-,20-,24-/m0/s1

Standard InChI Key:  HGDCMADSQGQRPQ-SKPFHBQLSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   26.0078   -8.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4329   -8.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8496   -8.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3292  -10.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1599  -10.8666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1895   -9.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4715   -9.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2667  -10.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5873  -10.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7379  -10.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1566   -9.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4286   -9.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2810  -10.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8636  -11.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9930   -9.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7108  -10.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4372   -9.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6982  -10.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3215  -11.3434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1882   -9.3458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.5594  -11.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1418  -12.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3038   -8.8410    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.3271  -12.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9096  -12.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5443  -12.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1305  -13.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3115  -13.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0523  -14.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7112  -14.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3774  -14.4718    0.0000 O   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
 11 23  1  0
 22 24  2  0
 24 25  1  0
 25 28  2  0
 27 26  2  0
 26 22  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347542

   ---

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: 454.41

Molecular Weight (Monoisotopic): 453.1303

AlogP: 6.58

#Rotatable Bonds: 4

Polar Surface Area: 21.70

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.81

CX LogP: 6.38

CX LogD: 5.83

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: 0.24

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