1-Isopropyl5-methyl4-isopropyl-6-(3-nitrophenyl)-2-oxo-2,3-dihydropyrimidine-1,5(6H)-dicarboxylate

ID: ALA2398420

Max Phase: Preclinical

Molecular Formula: C19H23N3O7

Molecular Weight: 405.41

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  ZHQUFYKOKIITMM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   16.2037  -25.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4891  -25.6108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747  -25.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747  -24.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4891  -23.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2037  -24.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9181  -23.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6326  -24.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9181  -23.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -23.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -23.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3457  -24.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9181  -25.6108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4891  -23.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747  -22.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747  -21.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4891  -21.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2037  -21.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2037  -22.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -21.4857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -20.6608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3457  -21.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -25.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3457  -25.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602  -26.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6312  -23.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6326  -22.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6326  -21.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3471  -23.1358    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  2  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  6  7  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
  1 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  2  0
 20 22  1  0
 16 20  1  0
  5 14  1  0
 23 24  1  0
 23 25  1  0
  3 23  1  0
 12 26  1  0
 27 28  1  0
 27 29  1  0
  9 27  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2398420

   ---

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: 3.29

#Rotatable Bonds: 5

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: 12.34

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.76

References

1. Kang S, Cooper G, Dunne SF, Luan CH, James Surmeier D, Silverman RB..  (2013)  Antagonism of L-type Ca2+ channels CaV1.3 and CaV1.2 by 1,4-dihydropyrimidines and 4H-pyrans as dihydropyridine mimics.,  21  (14): [PMID:23688558] [10.1016/j.bmc.2013.04.054]

Source

Source(1):

• Scientific Literature