(+/-)-3-(1S,4R,9S)-5-Bromo-3,3-dimethyl-9-(2-methylallyl)-1,2,3,4-tetrahydro-1,4-(epimino-methano)naphthalen-10-yl)methyl)-5-methylisoxazole

ID: ALA3347543

PubChem CID: 118718021

Max Phase: Preclinical

Molecular Formula: C22H27BrN2O

Molecular Weight: 415.38

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)N1Cc1cc(C)on1

Standard InChI:  InChI=1S/C22H27BrN2O/c1-13(2)9-18-21-20-16(7-6-8-17(20)23)19(11-22(21,4)5)25(18)12-15-10-14(3)26-24-15/h6-8,10,18-19,21H,1,9,11-12H2,2-5H3/t18-,19-,21-/m0/s1

Standard InChI Key:  WKNXZUINXIXXGC-ZJOUEHCJSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   17.3489   -0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7740   -1.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1907   -0.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6703   -2.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5009   -3.3179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5305   -1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8126   -2.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6078   -2.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9284   -3.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0790   -2.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4977   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7696   -2.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6221   -3.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2046   -3.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3341   -2.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0519   -2.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7783   -2.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0392   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6626   -3.7947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5293   -1.7971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9005   -4.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4829   -4.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6449   -1.2923    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.6707   -4.8119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4906   -5.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8072   -5.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1933   -6.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2687   -6.8364    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
 11 23  1  0
 22 24  2  0
 24 25  1  0
 25 27  1  0
 26 22  1  0
 26 27  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347543

   ---

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: 415.38

Molecular Weight (Monoisotopic): 414.1307

AlogP: 6.15

#Rotatable Bonds: 4

Polar Surface Area: 29.27

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.63

CX LogP: 5.40

CX LogD: 5.33

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -0.36

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