(-)-(R)-5-isopropyl 1-methyl 4-methyl-6-(3-nitrophenyl)-2-oxo-2,3-dihydropyrimidine-1,5(6H)-dicarboxylate

ID: ALA2398402

Max Phase: Preclinical

Molecular Formula: C17H19N3O7

Molecular Weight: 377.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N1C(=O)NC(C)=C(C(=O)OC(C)C)[C@H]1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H19N3O7/c1-9(2)27-15(21)13-10(3)18-16(22)19(17(23)26-4)14(13)11-6-5-7-12(8-11)20(24)25/h5-9,14H,1-4H3,(H,18,22)/t14-/m1/s1

Standard InChI Key:  KYAYYORCSGKDDP-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   18.2183  -26.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5134  -27.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8043  -26.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8043  -26.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5134  -25.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2183  -26.0196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9275  -25.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9275  -24.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6366  -26.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -25.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -24.7938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3902  -26.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9275  -27.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5134  -24.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8043  -24.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8043  -23.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5134  -23.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2183  -23.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2183  -24.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -23.1593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -22.3422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3902  -23.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -27.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6812  -25.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9719  -26.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6812  -24.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6366  -26.8368    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  1
  3 23  1  0
 24 25  1  0
 24 26  1  0
 12 24  1  0
  9 27  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2398402

   ---

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: 2.65

#Rotatable Bonds: 4

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: 12.39

CX Basic pKa: ┄

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.99

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