3-(2,4-dimethoxypyrimidin-5-yl)quinoline-5,8-dicarboxylic acid

ID: ALA5290257

Max Phase: Preclinical

Molecular Formula: C17H13N3O6

Molecular Weight: 355.31

Names and Identifiers

Canonical SMILES:  COc1ncc(-c2cnc3c(C(=O)O)ccc(C(=O)O)c3c2)c(OC)n1

Standard InChI:  InChI=1S/C17H13N3O6/c1-25-14-12(7-19-17(20-14)26-2)8-5-11-9(15(21)22)3-4-10(16(23)24)13(11)18-6-8/h3-7H,1-2H3,(H,21,22)(H,23,24)

Standard InChI Key:  CAGSRYBLIZYFGG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -2.8435    0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230   -0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    1.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435    1.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203    1.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -1.2326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.6413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320    1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320    0.4127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247   -0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435    1.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435    2.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    1.6432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129    1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -2.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -2.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  4 13  1  0
 11 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 14 19  1  0
 17 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  1  0
  3 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290257

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.31

Molecular Weight (Monoisotopic): 355.0804

AlogP: 2.11

#Rotatable Bonds: 5

Polar Surface Area: 131.73

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.43

CX Basic pKa: 2.83

CX LogP: 1.65

CX LogD: -4.52

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -0.41

References

1. Van de Walle T, Cools L, Mangelinckx S, D'hooghe M..  (2021)  Recent contributions of quinolines to antimalarial and anticancer drug discovery research.,  226  [PMID:34655985] [10.1016/j.ejmech.2021.113865]

Source

Source(1):

• Scientific Literature