methyl 6-(3-(1-methylindolin-5-yl)ureido)-4-oxo-1,4-dihydroquinoline-2-carboxylate

ID: ALA4205078

PubChem CID: 145977845

Max Phase: Preclinical

Molecular Formula: C21H20N4O4

Molecular Weight: 392.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(=O)c2cc(NC(=O)Nc3ccc4c(c3)CCN4C)ccc2[nH]1

Standard InChI:  InChI=1S/C21H20N4O4/c1-25-8-7-12-9-13(4-6-18(12)25)22-21(28)23-14-3-5-16-15(10-14)19(26)11-17(24-16)20(27)29-2/h3-6,9-11H,7-8H2,1-2H3,(H,24,26)(H2,22,23,28)

Standard InChI Key:  YZQQPNXNHQMAKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    4.1025  -10.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9365   -9.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9353  -10.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6434  -10.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6416   -9.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3502   -9.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536  -10.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0620  -10.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7716  -10.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7683   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0553   -9.2964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0642  -11.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4747   -9.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4722   -8.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1837   -9.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1862  -10.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2273  -10.9430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199  -10.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5205   -9.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8119  -10.9419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -9.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892  -10.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984  -10.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -9.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3977   -9.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2329   -8.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4150   -8.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -9.1579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -9.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  2  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  3 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  1  1  0
  1 21  2  0
 21 25  1  0
 24 22  1  0
 22 23  2  0
 23  1  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205078

   ---

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: 392.42

Molecular Weight (Monoisotopic): 392.1485

AlogP: 2.95

#Rotatable Bonds: 3

Polar Surface Area: 103.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.79

CX Basic pKa: 3.74

CX LogP: 3.25

CX LogD: 2.63

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -1.06

References

1. Ling T, Lang W, Feng X, Das S, Maier J, Jeffries C, Shelat A, Rivas F..  (2018)  Novel vitexin-inspired scaffold against leukemia.,  146  [PMID:29407975] [10.1016/j.ejmech.2018.01.004]

Source

Source(1):

• Scientific Literature