(+)-(S)-diisopropyl 4-methyl-6-(3-nitrophenyl)-2-oxo-2,3-dihydropyrimidine-1,5(6H)-dicarboxylate

ID: ALA2398407

Max Phase: Preclinical

Molecular Formula: C19H23N3O7

Molecular Weight: 405.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)OC(C)C)[C@H](c2cccc([N+](=O)[O-])c2)N(C(=O)OC(C)C)C(=O)N1

Standard InChI:  InChI=1S/C19H23N3O7/c1-10(2)28-17(23)15-12(5)20-18(24)21(19(25)29-11(3)4)16(15)13-7-6-8-14(9-13)22(26)27/h6-11,16H,1-5H3,(H,20,24)/t16-/m0/s1

Standard InChI Key:  MSKZFZOPRWQKKK-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   30.2207  -17.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1384  -17.9751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0562  -17.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0562  -16.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1384  -15.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2207  -16.1005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3031  -15.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3854  -16.1005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3031  -14.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9738  -15.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9738  -14.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8915  -16.1005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3031  -17.9751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1384  -14.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0562  -13.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0562  -12.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1384  -11.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2207  -12.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2207  -13.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9738  -11.7263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9738  -10.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8915  -12.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9738  -17.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8092  -15.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7268  -16.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8092  -14.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3854  -13.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3854  -12.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4676  -14.2259    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  6
  3 23  1  0
 24 25  1  0
 24 26  1  0
 12 24  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:

   

   ALA2398407

   ---

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: 3.43

#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: 12.39

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.96

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