Ethyl 3-[2-(aminocarbonyl)ethyl]-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4087415

PubChem CID: 137643403

Max Phase: Preclinical

Molecular Formula: C17H20N4O6

Molecular Weight: 376.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)N(CCC(N)=O)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H20N4O6/c1-3-27-16(23)14-10(2)19-17(24)20(8-7-13(18)22)15(14)11-5-4-6-12(9-11)21(25)26/h4-6,9,15H,3,7-8H2,1-2H3,(H2,18,22)(H,19,24)

Standard InChI Key:  PUJADXSDBUCQPL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    9.3003  -14.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3157  -13.3692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6144  -12.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8998  -13.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8865  -14.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5857  -14.5802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1985  -12.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839  -13.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2139  -12.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0016  -14.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6277  -12.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424  -11.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3577  -10.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6564  -10.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9418  -10.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9285  -11.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0723  -10.5215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7716  -10.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856   -9.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1719  -14.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0303  -12.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7296  -13.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4442  -12.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1454  -13.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4595  -12.1799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126  -11.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259  -10.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
  1 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  2  0
 17 19  1  0
 13 17  1  0
  3 11  1  0
  5 20  1  0
 21 22  1  0
 23 24  2  0
 23 25  1  0
 22 23  1  0
  2 21  1  0
 26 27  1  0
  9 26  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4087415

   ---

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: 376.37

Molecular Weight (Monoisotopic): 376.1383

AlogP: 1.37

#Rotatable Bonds: 7

Polar Surface Area: 144.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 0.31

CX LogD: 0.31

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -1.32

References

1. Teleb M, Zhang FX, Farghaly AM, Aboul Wafa OM, Fronczek FR, Zamponi GW, Fahmy H..  (2017)  Synthesis of new N3-substituted dihydropyrimidine derivatives as L-/T- type calcium channel blockers.,  134  [PMID:28399450] [10.1016/j.ejmech.2017.03.080]

Source

Source(1):

• Scientific Literature