1-(4-Chlorophenethyl)-3-((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA2381044

Max Phase: Preclinical

Molecular Formula: C22H27ClN2O3

Molecular Weight: 402.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H]2CC[C@@]1(C)[C@@H](N1C(=O)CC(=O)N(CCc3ccc(Cl)cc3)C1=O)C2

Standard InChI:  InChI=1S/C22H27ClN2O3/c1-21(2)15-8-10-22(21,3)17(12-15)25-19(27)13-18(26)24(20(25)28)11-9-14-4-6-16(23)7-5-14/h4-7,15,17H,8-13H2,1-3H3/t15-,17+,22+/m1/s1

Standard InChI Key:  YYHKGMNCVMPCGZ-ZWWNWMABSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.5375  -17.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542  -17.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666  -17.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803  -19.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5137  -18.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012  -18.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929  -19.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304  -18.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5596  -19.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417  -17.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417  -18.5005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538  -18.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658  -18.5005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658  -17.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538  -17.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6815  -17.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6797  -18.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3948  -18.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087  -18.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1045  -19.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8176  -20.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5337  -19.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5322  -18.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8186  -18.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834  -17.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376  -16.8504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2481  -20.1536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2538  -19.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929  -19.9703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  6  5  1  0
  7  4  1  0
  7  2  1  0
  6  2  1  0
  6  8  1  0
  8  9  1  0
  7  9  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 11  1  1
  6 25  1  1
 10 26  2  0
 22 27  1  0
 12 28  2  0
  7 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2381044

   ---

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: 402.92

Molecular Weight (Monoisotopic): 402.1710

AlogP: 4.28

#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: 4.30

CX LogD: 1.97

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.06

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