1-(3-Chlorophenethyl)-3-((1S,2S)-2-hydroxycyclopentyl)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA2380890

Max Phase: Preclinical

Molecular Formula: C17H19ClN2O4

Molecular Weight: 350.80

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H19ClN2O4/c18-12-4-1-3-11(9-12)7-8-19-15(22)10-16(23)20(17(19)24)13-5-2-6-14(13)21/h1,3-4,9,13-14,21H,2,5-8,10H2/t13-,14-/m0/s1

Standard InChI Key:  AFSYFLRSPIQRJM-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.5792   -6.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -7.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913   -7.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032   -7.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032   -6.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913   -5.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8635   -5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7190   -5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7172   -7.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323   -7.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1461   -7.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1420   -8.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8549   -8.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5710   -8.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5696   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8560   -7.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2832   -7.1223    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9063   -7.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1260   -7.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -7.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1037   -8.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925   -8.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843   -6.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913   -8.3584    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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18  2  1  1
 19 23  1  6
  3 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2380890

   ---

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: 1.98

#Rotatable Bonds: 4

Polar Surface Area: 77.92

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.00

CX Basic pKa: ┄

CX LogP: 2.07

CX LogD: -0.26

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.61

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