cis-1-(4-Chlorophenethyl)-3-(((1R,2S,5R)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)pyrimi-dine-2,4,6(1H,3H,5H)-trione

ID: ALA2381045

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@H](CN3C(=O)CC(=O)N(CCc4ccc(Cl)cc4)C3=O)[C@H]1C2

Standard InChI:  InChI=1S/C22H27ClN2O3/c1-22(2)16-6-5-15(18(22)11-16)13-25-20(27)12-19(26)24(21(25)28)10-9-14-3-7-17(23)8-4-14/h3-4,7-8,15-16,18H,5-6,9-13H2,1-2H3/t15-,16-,18-/m1/s1

Standard InChI Key:  DHCUZFWNXIADAL-JFIYKMOQSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   11.6962  -19.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1130  -18.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875  -18.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9713  -18.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9713  -18.9465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6834  -19.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955  -18.9465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955  -18.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6834  -17.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2556  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1112  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1093  -19.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8244  -18.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5383  -19.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5342  -20.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2473  -20.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9634  -20.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9618  -19.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2483  -18.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2575  -19.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5424  -18.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5434  -18.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8324  -17.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1161  -18.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8309  -19.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8254  -18.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6777  -20.5997    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.6834  -20.1799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8309  -20.1905    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4016  -17.7110    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
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  2  0
  8 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  5 20  1  0
 21 20  1  6
 21 22  1  0
 25 21  1  0
 22 23  1  0
 24 23  1  0
 24  2  1  0
 25  2  1  0
 25 26  1  0
 24 26  1  0
 17 27  1  0
  6 28  2  0
 25 29  1  1
 24 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2381045

   ---

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: 4.14

#Rotatable Bonds: 5

Polar Surface Area: 57.69

Molecular Species: ACID

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.01

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 1.83

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: 0.09

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