methyl 1-(allylcarbamoyl)-6-(3-allylureido)-4-oxo-1,4-dihydroquinoline-2-carboxylate

ID: ALA4211234

PubChem CID: 145965505

Max Phase: Preclinical

Molecular Formula: C19H20N4O5

Molecular Weight: 384.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCNC(=O)Nc1ccc2c(c1)c(=O)cc(C(=O)OC)n2C(=O)NCC=C

Standard InChI:  InChI=1S/C19H20N4O5/c1-4-8-20-18(26)22-12-6-7-14-13(10-12)16(24)11-15(17(25)28-3)23(14)19(27)21-9-5-2/h4-7,10-11H,1-2,8-9H2,3H3,(H,21,27)(H2,20,22,26)

Standard InChI Key:  GOVLEFUFZYVTDC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.4412  -15.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400  -16.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1481  -16.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1463  -15.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8549  -15.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8583  -16.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667  -16.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2764  -16.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2730  -15.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5600  -15.0745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5689  -17.5330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9794  -15.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9769  -14.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6884  -15.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6909  -16.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7320  -16.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246  -16.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0253  -15.4948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166  -16.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6092  -16.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012  -16.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1938  -16.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5555  -14.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2610  -13.8448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2565  -13.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9619  -12.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6719  -13.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8456  -13.8526    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
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 10 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 23 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4211234

   ---

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: 384.39

Molecular Weight (Monoisotopic): 384.1434

AlogP: 1.84

#Rotatable Bonds: 6

Polar Surface Area: 118.53

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.10

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