3-[5-(Ethoxycarbonyl)-4-methyl-6-(3-nitrophenyl)-2-oxo-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid

ID: ALA4094921

PubChem CID: 137654304

Max Phase: Preclinical

Molecular Formula: C17H19N3O7

Molecular Weight: 377.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H19N3O7/c1-3-27-16(23)14-10(2)18-17(24)19(8-7-13(21)22)15(14)11-5-4-6-12(9-11)20(25)26/h4-6,9,15H,3,7-8H2,1-2H3,(H,18,24)(H,21,22)

Standard InChI Key:  MGTYQRRJACHXHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   13.6302  -13.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9211  -13.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2162  -13.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6302  -12.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3393  -13.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071  -14.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7980  -14.6938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930  -14.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930  -13.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7980  -13.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071  -13.4680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2162  -14.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7980  -12.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930  -11.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930  -11.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7980  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071  -11.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071  -11.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3839  -10.6078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3839   -9.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748  -11.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3839  -14.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3839  -13.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3839  -12.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748  -13.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658  -13.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2608  -13.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  6 11  1  0
  6 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  2  0
 19 21  1  0
 15 19  1  0
 10 13  1  0
  8 22  1  0
 23 24  2  0
 26 27  1  0
 25 26  1  0
 23 25  1  0
  9 23  1  0
  3 11  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4094921

   ---

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: 377.35

Molecular Weight (Monoisotopic): 377.1223

AlogP: 1.97

#Rotatable Bonds: 7

Polar Surface Area: 139.08

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: -2.22

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -1.13

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