2-((1-(2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)-N-(p-nitrophenyl)benzamide

ID: ALA4085950

PubChem CID: 137644305

Max Phase: Preclinical

Molecular Formula: C29H30N6O6

Molecular Weight: 558.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCn1cc(COc3ccccc3C(=O)Nc3ccc([N+](=O)[O-])cc3)nn1)CC2

Standard InChI:  InChI=1S/C29H30N6O6/c1-39-27-15-20-11-12-33(17-21(20)16-28(27)40-2)13-14-34-18-23(31-32-34)19-41-26-6-4-3-5-25(26)29(36)30-22-7-9-24(10-8-22)35(37)38/h3-10,15-16,18H,11-14,17,19H2,1-2H3,(H,30,36)

Standard InChI Key:  RSQNTVHEMXDATL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   20.3499  -28.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3488  -29.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0610  -29.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7748  -29.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7719  -28.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0592  -28.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4872  -29.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4885  -30.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1943  -29.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9068  -29.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4822  -28.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1915  -28.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9018  -28.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6511  -28.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1998  -27.8097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7844  -27.0994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9816  -27.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0180  -27.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4263  -27.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2476  -27.0968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6573  -27.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4751  -27.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6554  -26.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4794  -26.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8843  -27.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7045  -27.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1208  -26.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7068  -25.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8879  -25.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1199  -24.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9421  -26.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3487  -27.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9413  -24.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9034  -30.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6151  -30.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3273  -30.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3233  -29.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6111  -29.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0384  -30.9617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7446  -30.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0415  -31.7789    0.0000 O   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
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 23  1  0
 21 22  1  0
 22 25  1  0
 24 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 30 33  1  0
 10 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 10  1  0
 39 40  2  0
 39 41  1  0
 36 39  1  0
M  CHG  2  39   1  41  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4085950

   ---

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: 558.60

Molecular Weight (Monoisotopic): 558.2227

AlogP: 4.09

#Rotatable Bonds: 11

Polar Surface Area: 133.88

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.14

CX LogP: 4.17

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: -1.65

References

1. Pan M, Cui J, Jiao L, Ghaleb H, Liao C, Zhou J, Kairuki M, Lin H, Huang W, Qian H..  (2017)  Synthesis and biological evaluation of JL-A7 derivatives as potent ABCB1 inhibitors.,  25  (15): [PMID:28645831] [10.1016/j.bmc.2017.06.015]

Source

Source(1):

• Scientific Literature