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

ID: ALA2381041

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)N1CCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C17H19ClN2O4/c18-13-5-3-12(4-6-13)7-8-19-15(21)10-16(22)20(17(19)23)11-14-2-1-9-24-14/h3-6,14H,1-2,7-11H2/t14-/m1/s1

Standard InChI Key:  NPTQLWJTMWYFPR-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.4042  -13.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042  -14.8087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163  -15.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8283  -14.8087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8283  -13.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163  -13.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885  -13.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440  -13.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422  -15.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573  -14.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9711  -15.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9670  -16.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6801  -16.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3962  -16.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3947  -15.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6811  -14.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6902  -15.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082  -14.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9805  -13.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884  -13.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242  -14.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296  -15.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1106  -16.4618    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1163  -16.0420    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
  2 17  1  0
 18 17  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 14 23  1  0
  3 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2381041

   ---

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: -0.91

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