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

ID: ALA4084057

PubChem CID: 137645149

Max Phase: Preclinical

Molecular Formula: C22H26F3N3O4

Molecular Weight: 453.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCCCNc1ccc([N+](=O)[O-])c(C(F)(F)F)c1)CC2

Standard InChI:  InChI=1S/C22H26F3N3O4/c1-31-20-11-15-7-10-27(14-16(15)12-21(20)32-2)9-4-3-8-26-17-5-6-19(28(29)30)18(13-17)22(23,24)25/h5-6,11-13,26H,3-4,7-10,14H2,1-2H3

Standard InChI Key:  KMLBJUJNEUQEJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   23.3463  -14.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3452  -14.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0532  -15.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7629  -14.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7600  -14.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0514  -13.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4683  -13.6659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4653  -12.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1776  -14.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6371  -15.3096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4712  -15.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4725  -16.1258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.1783  -14.8989    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.1749  -15.7165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.9298  -14.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2217  -15.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5143  -14.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8063  -15.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0989  -14.8982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0799  -14.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3650  -13.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4071  -15.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6916  -14.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6696  -14.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9486  -13.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2491  -14.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2752  -14.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9966  -15.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5809  -15.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8605  -15.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5296  -13.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8343  -14.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  7  9  1  0
  5  7  1  0
  2 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 22  1  0
 20 21  1  0
 21 24  1  0
 23 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 29 30  1  0
 26 31  1  0
 31 32  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4084057

   ---

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: 453.46

Molecular Weight (Monoisotopic): 453.1875

AlogP: 4.88

#Rotatable Bonds: 9

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: 8.23

CX LogP: 4.31

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -1.20

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