Ethyl 3-(2-cyanoethyl)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4103790

PubChem CID: 137656625

Max Phase: Preclinical

Molecular Formula: C17H18N4O5

Molecular Weight: 358.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N4O5/c1-3-26-16(22)14-11(2)19-17(23)20(9-5-8-18)15(14)12-6-4-7-13(10-12)21(24)25/h4,6-7,10,15H,3,5,9H2,1-2H3,(H,19,23)

Standard InChI Key:  UJZWRUVZABWVRL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    6.3186  -13.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072  -12.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5946  -12.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933  -12.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006  -13.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132  -13.7268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807  -12.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4753  -12.5248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1694  -11.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0312  -13.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833  -11.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2845  -10.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2773  -10.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -9.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593  -10.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707  -10.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9786   -9.6228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9673   -8.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6912  -10.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993  -13.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0085  -12.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7211  -12.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7325  -13.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7438  -14.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568  -10.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454  -10.0735    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  3  0
 22 23  1  0
  2 21  1  0
 25 26  1  0
  9 25  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4103790

   ---

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: 358.35

Molecular Weight (Monoisotopic): 358.1277

AlogP: 2.41

#Rotatable Bonds: 6

Polar Surface Area: 125.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.18

CX LogD: 1.18

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -1.47

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