6-Isopropyl-5-(methoxycarbonyl)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

ID: ALA2398411

Max Phase: Preclinical

Molecular Formula: C15H17N3O5

Molecular Weight: 319.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C(C)C)NC(=O)NC1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H17N3O5/c1-8(2)12-11(14(19)23-3)13(17-15(20)16-12)9-5-4-6-10(7-9)18(21)22/h4-8,13H,1-3H3,(H2,16,17,20)

Standard InChI Key:  HVTWQRXLPHDMEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   16.9248   -5.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9443   -4.7275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2397   -4.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5157   -4.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4962   -5.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2007   -5.9478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6293   -5.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2591   -3.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9831   -3.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0026   -2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2980   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5740   -2.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5545   -3.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7266   -1.8576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4312   -2.2869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7460   -1.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8111   -4.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0871   -4.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8306   -3.4397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1260   -3.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7722   -5.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0676   -5.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7527   -6.7389    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
 17 18  2  0
 19 20  1  0
 17 19  1  0
  4 17  1  0
 21 22  1  0
 21 23  1  0
  5 21  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2398411

   ---

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: 319.32

Molecular Weight (Monoisotopic): 319.1168

AlogP: 2.03

#Rotatable Bonds: 4

Polar Surface Area: 110.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.43

CX Basic pKa: ┄

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: -0.91

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