1,3-Dimethoxycarbonyl-5-(isopropyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

ID: ALA2398423

PubChem CID: 71722882

Max Phase: Preclinical

Molecular Formula: C19H21N3O9

Molecular Weight: 435.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N1C(=O)N(C(=O)OC)C(c2cccc([N+](=O)[O-])c2)C(C(=O)OC(C)C)=C1C

Standard InChI:  InChI=1S/C19H21N3O9/c1-10(2)31-16(23)14-11(3)20(18(25)29-4)17(24)21(19(26)30-5)15(14)12-7-6-8-13(9-12)22(27)28/h6-10,15H,1-5H3

Standard InChI Key:  XBHIDAKVJKFMAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   19.0781  -18.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1087  -18.0395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4100  -17.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6807  -17.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6501  -18.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3488  -19.2496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7768  -19.3027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4407  -16.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1700  -16.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2006  -15.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5019  -15.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7726  -15.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7420  -16.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9298  -15.1804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9604  -14.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6285  -15.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9208  -19.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9821  -17.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2527  -17.9335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0127  -16.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3140  -16.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3446  -15.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5847  -16.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8380  -17.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8687  -16.8293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5367  -18.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5061  -18.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3182  -20.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5890  -20.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0169  -20.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7462  -20.1271    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
  1  7  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  2  0
 14 16  1  0
 10 14  1  0
  3  8  1  0
  5 17  1  0
 18 19  2  0
 21 22  1  0
 21 23  1  0
 20 21  1  0
 18 20  1  0
  4 18  1  0
 24 25  2  0
 26 27  1  0
 24 26  1  0
  2 24  1  0
 28 29  2  0
 30 31  1  0
 28 30  1  0
  6 28  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2398423

   1-O,3-O-dimethyl 5-O-propan-2-yl 6-methyl-4-(3-nitrophenyl)-2-oxo-4H-pyrimidine-1,3,5-tricarboxylate

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: 435.39

Molecular Weight (Monoisotopic): 435.1278

AlogP: 3.13

#Rotatable Bonds: 4

Polar Surface Area: 145.59

Molecular Species: ┄

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.86

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