N-(2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-4-nitro-3-(trifluoromethyl)aniline

ID: ALA4079680

PubChem CID: 137650821

Max Phase: Preclinical

Molecular Formula: C20H22F3N3O4

Molecular Weight: 425.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCNc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)CC2

Standard InChI:  InChI=1S/C20H22F3N3O4/c1-29-18-9-13-5-7-25(12-14(13)10-19(18)30-2)8-6-24-15-3-4-17(26(27)28)16(11-15)20(21,22)23/h3-4,9-11,24H,5-8,12H2,1-2H3

Standard InChI Key:  WFVGVXWSQSKGEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   19.7219   -3.6981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7267   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0234   -2.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0182   -4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5539   -2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5527   -3.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2608   -4.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9704   -3.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9676   -2.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2590   -2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6759   -2.4646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6728   -1.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3852   -2.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8447   -4.1083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6788   -4.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6801   -4.9245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.3859   -3.6976    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.3825   -4.5152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.1373   -3.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4293   -4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3138   -3.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3160   -2.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6068   -2.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8950   -2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8967   -3.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6065   -4.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1900   -4.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4813   -3.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1872   -2.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4796   -2.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3 22  1  0
 21  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 11 13  1  0
  9 11  1  0
  6 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 20  1  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
 27 28  1  0
 24 29  1  0
 29 30  1  0
M  CHG  2  11   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4079680

   ---

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: 425.41

Molecular Weight (Monoisotopic): 425.1562

AlogP: 4.10

#Rotatable Bonds: 7

Polar Surface Area: 76.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.35

CX LogP: 3.73

CX LogD: 3.46

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -1.29

References

1. Amata E, Dichiara M, Arena E, Pittalà V, Pistarà V, Cardile V, Graziano ACE, Fraix A, Marrazzo A, Sortino S, Prezzavento O..  (2017)  Novel Sigma Receptor Ligand-Nitric Oxide Photodonors: Molecular Hybrids for Double-Targeted Antiproliferative Effect.,  60  (23): [PMID:29172528] [10.1021/acs.jmedchem.7b00791]

Source

Source(1):

• Scientific Literature