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

ID: ALA4084433

PubChem CID: 137645877

Max Phase: Preclinical

Molecular Formula: C19H23N3O7

Molecular Weight: 405.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CCN1C(=O)NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C19H23N3O7/c1-4-28-15(23)9-10-21-17(13-7-6-8-14(11-13)22(26)27)16(18(24)29-5-2)12(3)20-19(21)25/h6-8,11,17H,4-5,9-10H2,1-3H3,(H,20,25)

Standard InChI Key:  KRBHMFWNDJTJEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    9.2632  -14.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507  -13.5153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5364  -13.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8347  -13.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8473  -14.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5615  -14.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204  -13.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4187  -13.5540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1100  -12.3205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9754  -14.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5238  -12.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2255  -11.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2151  -11.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5008  -10.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7991  -11.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8117  -11.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9168  -10.6452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -9.8269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6289  -11.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456  -14.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524  -13.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6666  -13.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3683  -13.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3558  -12.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0805  -13.4731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7822  -13.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4965  -13.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3957  -11.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3831  -11.1027    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
 26 27  1  0
 25 26  1  0
 23 25  1  0
 22 23  1  0
  2 21  1  0
 28 29  1  0
  9 28  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4084433

   ---

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: 405.41

Molecular Weight (Monoisotopic): 405.1536

AlogP: 2.45

#Rotatable Bonds: 8

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: 1.62

CX LogD: 1.62

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.18

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