trans-(1S,2S)-2-(3-(3-Chlorophenethyl)-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)cyclopentyl acetate

ID: ALA2380892

Max Phase: Preclinical

Molecular Formula: C19H21ClN2O5

Molecular Weight: 392.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1CCC[C@@H]1N1C(=O)CC(=O)N(CCc2cccc(Cl)c2)C1=O

Standard InChI:  InChI=1S/C19H21ClN2O5/c1-12(23)27-16-7-3-6-15(16)22-18(25)11-17(24)21(19(22)26)9-8-13-4-2-5-14(20)10-13/h2,4-5,10,15-16H,3,6-9,11H2,1H3/t15-,16-/m0/s1

Standard InChI Key:  SYLGZJOGNOSQOG-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   21.7092   -6.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7092   -7.0461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4212   -7.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1333   -7.0461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1333   -6.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4212   -5.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9935   -5.8106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8490   -5.8106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8472   -7.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5623   -7.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2762   -7.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2720   -8.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9851   -8.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7012   -8.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6998   -7.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9861   -7.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4134   -7.0433    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0362   -7.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2560   -7.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7600   -7.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2337   -8.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0224   -8.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0142   -6.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2102   -6.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9684   -5.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6479   -6.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4212   -8.2795    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
 23 24  1  0
 24 25  1  0
 24 26  2  0
  3 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2380892

   ---

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: 392.84

Molecular Weight (Monoisotopic): 392.1139

AlogP: 2.55

#Rotatable Bonds: 5

Polar Surface Area: 83.99

Molecular Species: ACID

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.00

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -0.40

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