ethyl 4-((4-aminophenyl)ethynyl)-6-methoxyquinoline-2-carboxylate

ID: ALA4637708

PubChem CID: 156011178

Max Phase: Preclinical

Molecular Formula: C21H18N2O3

Molecular Weight: 346.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C#Cc2ccc(N)cc2)c2cc(OC)ccc2n1

Standard InChI:  InChI=1S/C21H18N2O3/c1-3-26-21(24)20-12-15(7-4-14-5-8-16(22)9-6-14)18-13-17(25-2)10-11-19(18)23-20/h5-6,8-13H,3,22H2,1-2H3

Standard InChI Key:  RAWAYYZHLDKMKN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.2609  -22.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2598  -23.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9678  -24.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9660  -22.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6746  -22.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6754  -23.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3839  -24.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0922  -23.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0875  -22.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3784  -22.4510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7927  -22.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5029  -22.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7877  -21.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2081  -22.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9182  -22.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5517  -24.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8443  -23.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3856  -24.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3796  -25.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3736  -26.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6594  -26.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6531  -27.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3583  -28.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0714  -27.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0742  -26.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3533  -28.9859    0.0000 N   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
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 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
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637708

   ---

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: 346.39

Molecular Weight (Monoisotopic): 346.1317

AlogP: 3.40

#Rotatable Bonds: 3

Polar Surface Area: 74.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.92

CX LogP: 3.81

CX LogD: 3.81

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.77

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