ethyl 6-methoxy-4-((2-nitrophenyl)ethynyl)quinoline-2-carboxylate

ID: ALA4648478

PubChem CID: 156021770

Max Phase: Preclinical

Molecular Formula: C21H16N2O5

Molecular Weight: 376.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C#Cc2ccccc2[N+](=O)[O-])c2cc(OC)ccc2n1

Standard InChI:  InChI=1S/C21H16N2O5/c1-3-28-21(24)19-12-15(17-13-16(27-2)10-11-18(17)22-19)9-8-14-6-4-5-7-20(14)23(25)26/h4-7,10-13H,3H2,1-2H3

Standard InChI Key:  KPGQVNQLJZAUSE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.2114  -12.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2102  -13.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9183  -13.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9165  -12.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6251  -12.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6259  -13.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3344  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0427  -13.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0379  -12.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3288  -12.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7431  -12.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5022  -13.9889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4533  -12.7423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1585  -12.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8687  -12.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7382  -11.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7948  -13.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3361  -14.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3301  -15.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3240  -16.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6099  -16.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6035  -17.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3087  -18.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0218  -17.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0247  -16.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7357  -16.4357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7386  -15.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4420  -16.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
  2 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  2  0
 12 17  1  0
  7 18  1  0
 18 19  3  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 25 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4648478

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.37

Molecular Weight (Monoisotopic): 376.1059

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 91.56

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.15

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.96

References

1. Costa CA, Lopes RM, Ferraz LS, Esteves GNN, Di Iorio JF, Souza AA, de Oliveira IM, Manarin F, Judice WAS, Stefani HA, Rodrigues T..  (2020)  Cytotoxicity of 4-substituted quinoline derivatives: Anticancer and antileishmanial potential.,  28  (11): [PMID:32336669] [10.1016/j.bmc.2020.115511]

Source

Source(1):

• Scientific Literature