cis-(1S,3R)-3-(3-(3-chlorophenethyl)-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)cyclopentanecarboxylic acid

ID: ALA2380888

Max Phase: Preclinical

Molecular Formula: C18H19ClN2O5

Molecular Weight: 378.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CC[C@@H](N2C(=O)CC(=O)N(CCc3cccc(Cl)c3)C2=O)C1

Standard InChI:  InChI=1S/C18H19ClN2O5/c19-13-3-1-2-11(8-13)6-7-20-15(22)10-16(23)21(18(20)26)14-5-4-12(9-14)17(24)25/h1-3,8,12,14H,4-7,9-10H2,(H,24,25)/t12-,14+/m0/s1

Standard InChI Key:  AIPRKMQHUFVEPR-GXTWGEPZSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.9169   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9169   -1.4334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6289   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3409   -1.4334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3409   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6289   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2012   -0.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0566   -0.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0547   -1.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7698   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4838   -1.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4795   -2.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1926   -3.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9087   -2.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9073   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1936   -1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6208   -1.4307    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2440   -1.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4637   -1.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9677   -2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414   -2.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2301   -2.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1734   -3.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3634   -3.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7148   -4.3802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6289   -2.6667    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
 21 23  1  1
 23 24  1  0
 23 25  2  0
  3 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2380888

   ---

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: 378.81

Molecular Weight (Monoisotopic): 378.0982

AlogP: 2.32

#Rotatable Bonds: 5

Polar Surface Area: 94.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: -3.13

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.81

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