1-isopropyl 5-methyl 4-methyl-2-(methylthio)-6-(3-nitrophenyl)pyrimidine-1,5(6H)-dicarboxylate

ID: ALA2398397

PubChem CID: 71723172

Max Phase: Preclinical

Molecular Formula: C18H21N3O6S

Molecular Weight: 407.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O6S/c1-10(2)27-18(23)20-15(12-7-6-8-13(9-12)21(24)25)14(16(22)26-4)11(3)19-17(20)28-5/h6-10,15H,1-5H3

Standard InChI Key:  IAWAKCIJMCLLBY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   25.0738   -5.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0695   -4.8509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3529   -4.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6405   -4.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6448   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3614   -6.0920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9239   -4.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9196   -3.6245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2116   -4.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7903   -6.0847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.7946   -6.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9324   -6.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3486   -3.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0609   -3.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0567   -2.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3400   -1.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6277   -2.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6320   -3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7690   -1.9597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7648   -1.1347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4856   -2.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2158   -5.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7819   -4.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4984   -4.8435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7775   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2129   -4.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9273   -4.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2129   -3.6060    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  2  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
 10 11  1  0
  1 10  1  0
  5 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  2  0
 19 21  1  0
 15 19  1  0
  3 13  1  0
  9 22  1  0
 23 24  1  0
 23 25  2  0
  2 23  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2398397

   5-O-methyl 3-O-propan-2-yl 6-methyl-2-methylsulfanyl-4-(3-nitrophenyl)-4H-pyrimidine-3,5-dicarboxylate

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: 407.45

Molecular Weight (Monoisotopic): 407.1151

AlogP: 3.66

#Rotatable Bonds: 4

Polar Surface Area: 111.34

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.81

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -1.22

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