(R)-1-(3-Chlorophenethyl)-3-((tetrahydrofuran-2-yl)methyl)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA2381021

Max Phase: Preclinical

Molecular Formula: C17H19ClN2O4

Molecular Weight: 350.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(=O)N(C[C@H]2CCCO2)C(=O)N1CCc1cccc(Cl)c1

Standard InChI:  InChI=1S/C17H19ClN2O4/c18-13-4-1-3-12(9-13)6-7-19-15(21)10-16(22)20(17(19)23)11-14-5-2-8-24-14/h1,3-4,9,14H,2,5-8,10-11H2/t14-/m1/s1

Standard InChI Key:  KGTWIWDFJMQFRA-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.1669  -16.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1669  -16.8378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8790  -17.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5910  -16.8378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5910  -16.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8790  -15.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4512  -15.6024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3067  -15.6024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3049  -17.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0200  -16.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7338  -17.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7297  -18.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4428  -18.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1587  -18.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1573  -17.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4437  -16.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8710  -16.8351    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4529  -17.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7709  -16.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7432  -15.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511  -15.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4869  -16.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9923  -17.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8790  -18.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  2  0
  5  8  2  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
  2 18  1  0
 19 18  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19 23  1  0
  3 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2381021

   ---

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: 350.80

Molecular Weight (Monoisotopic): 350.1033

AlogP: 2.24

#Rotatable Bonds: 5

Polar Surface Area: 66.92

Molecular Species: ACID

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.00

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: -0.12

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -1.06

References

1. Kang S, Cooper G, Dunne SF, Luan CH, Surmeier DJ, Silverman RB..  (2013)  Structure-activity relationship of N,N'-disubstituted pyrimidinetriones as Ca(V)1.3 calcium channel-selective antagonists for Parkinson's disease.,  56  (11): [PMID:23651412] [10.1021/jm4005048]

Source

Source(1):

• Scientific Literature