Ethyl 3-(2-chlorophenyl)-5,7-dimethyl-2-(((methylcarbamoyl)oxy)methyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate

ID: ALA5290485

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O5

Molecular Weight: 443.89

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(C)cc2nc(COC(=O)NC)n(-c3ccccc3Cl)c(=O)c2c1C

Standard InChI:  InChI=1S/C22H22ClN3O5/c1-5-30-21(28)18-12(2)10-15-19(13(18)3)20(27)26(16-9-7-6-8-14(16)23)17(25-15)11-31-22(29)24-4/h6-10H,5,11H2,1-4H3,(H,24,29)

Standard InChI Key:  NUVXJFLCRWIOHW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -2.1335   -0.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -1.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    0.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219    1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102    0.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7102   -0.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.0291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -1.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -0.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451   -1.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5567   -0.6142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451   -1.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435    1.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    1.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203    1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7086    1.8467    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.4357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451    0.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567    0.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567   -0.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683   -1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451    1.4370    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
  5  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
  4 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 18  9  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
 23 24  1  0
  8 25  2  0
  2 26  1  0
  1 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290485

   ---

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: 443.89

Molecular Weight (Monoisotopic): 443.1248

AlogP: 3.69

#Rotatable Bonds: 5

Polar Surface Area: 99.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -1.00

References

1. Alagarsamy V, Chitra K, Saravanan G, Solomon VR, Sulthana MT, Narendhar B..  (2018)  An overview of quinazolines: Pharmacological significance and recent developments.,  151  [PMID:29656203] [10.1016/j.ejmech.2018.03.076]

Source

Source(1):

• Scientific Literature