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

ID: ALA2381013

Max Phase: Preclinical

Molecular Formula: C18H21ClN2O3

Molecular Weight: 348.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CCC(N2C(=O)CC(=O)N(CCc3cccc(Cl)c3)C2=O)C1

Standard InChI:  InChI=1S/C18H21ClN2O3/c1-12-5-6-15(9-12)21-17(23)11-16(22)20(18(21)24)8-7-13-3-2-4-14(19)10-13/h2-4,10,12,15H,5-9,11H2,1H3

Standard InChI Key:  PROGJMDSZVGORE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   20.2714   -4.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2643   -5.6731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9833   -6.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6954   -5.6834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6954   -4.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9833   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5557   -4.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4111   -4.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4092   -6.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1243   -5.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8383   -6.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8341   -6.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5471   -7.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2632   -6.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2618   -6.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5481   -5.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9754   -5.6807    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.5852   -6.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8069   -5.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3112   -6.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7751   -7.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5656   -6.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4864   -6.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9807   -6.9168    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
  2 18  1  0
 20 23  1  0
  3 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2381013

   ---

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: 348.83

Molecular Weight (Monoisotopic): 348.1241

AlogP: 3.25

#Rotatable Bonds: 4

Polar Surface Area: 57.69

Molecular Species: ACID

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.00

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 1.10

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -0.86

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