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

ID: ALA4062752

PubChem CID: 137635289

Max Phase: Preclinical

Molecular Formula: C18H21N3O7

Molecular Weight: 391.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O7/c1-4-28-17(23)15-11(2)19-18(24)20(9-8-14(22)27-3)16(15)12-6-5-7-13(10-12)21(25)26/h5-7,10,16H,4,8-9H2,1-3H3,(H,19,24)

Standard InChI Key:  HSIIIMALOYNLHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    9.6389  -14.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6459  -13.5874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9414  -13.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2299  -13.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2229  -14.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9274  -14.8077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5254  -13.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138  -13.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344  -12.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3414  -14.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484  -12.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6599  -11.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6689  -11.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9644  -10.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2529  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2459  -11.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3804  -10.7340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0829  -11.1469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3874   -9.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114  -14.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3574  -13.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620  -13.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7735  -13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7805  -12.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4760  -13.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4690  -14.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8299  -11.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8369  -11.1070    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
 25 26  1  0
 23 25  1  0
 22 23  1  0
  2 21  1  0
 27 28  1  0
  9 27  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4062752

   ---

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: 391.38

Molecular Weight (Monoisotopic): 391.1380

AlogP: 2.06

#Rotatable Bonds: 7

Polar Surface Area: 128.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -1.19

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