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

ID: ALA3347554

PubChem CID: 86301661

Max Phase: Preclinical

Molecular Formula: C23H25Cl2N

Molecular Weight: 386.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C[C@@H]1N[C@H]2CC(C)(C)[C@@H]1c1c(-c3ccc(Cl)c(Cl)c3)cccc12

Standard InChI:  InChI=1S/C23H25Cl2N/c1-13(2)10-19-22-21-15(14-8-9-17(24)18(25)11-14)6-5-7-16(21)20(26-19)12-23(22,3)4/h5-9,11,19-20,22,26H,1,10,12H2,2-4H3/t19-,20-,22-/m0/s1

Standard InChI Key:  VDDOYZHUPMVKNZ-ONTIZHBOSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.5400   -7.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3295   -8.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210   -8.4698    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
    3.2025   -8.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -8.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -7.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981   -7.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7672   -7.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -8.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1818   -6.8861    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6444   -6.3816    0.0000 Cl  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
 11 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 25 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347554

   (1R,8S,10S)-3-(3,4-dichlorophenyl)-11,11-dimethyl-10-(2-methylprop-2-enyl)-9-azatricyclo[6.2.2.02,7]dodeca-2,4,6-triene

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: 386.37

Molecular Weight (Monoisotopic): 385.1364

AlogP: 7.15

#Rotatable Bonds: 3

Polar Surface Area: 12.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.31

CX LogP: 6.73

CX LogD: 4.84

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

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