(S)-Methyl 2-(3-cyclopentyl-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)-3-phenylpropanoate

ID: ALA2380914

Max Phase: Preclinical

Molecular Formula: C19H22N2O5

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccccc1)N1C(=O)CC(=O)N(C2CCCC2)C1=O

Standard InChI:  InChI=1S/C19H22N2O5/c1-26-18(24)15(11-13-7-3-2-4-8-13)21-17(23)12-16(22)20(19(21)25)14-9-5-6-10-14/h2-4,7-8,14-15H,5-6,9-12H2,1H3/t15-/m0/s1

Standard InChI Key:  FUQYXCZINJLBFV-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.1397  -14.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639  -12.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639  -13.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770  -14.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901  -13.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901  -12.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770  -12.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472  -12.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898  -14.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088  -13.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6149  -14.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0865  -15.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760  -15.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2770  -14.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055  -14.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4107  -13.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7070  -12.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105  -14.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9968  -15.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279  -15.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037  -16.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1779  -14.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060  -15.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6036  -14.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5643  -14.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317  -13.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  8  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  9  3  1  0
  4 14  2  0
  5 15  1  0
 15 16  1  0
 16  1  1  0
  6 17  2  0
 15 18  1  1
 18 19  1  0
 18 20  2  0
 19 21  1  0
  1 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2380914

   ---

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: 358.39

Molecular Weight (Monoisotopic): 358.1529

AlogP: 1.89

#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: 4.98

CX Basic pKa: ┄

CX LogP: 2.38

CX LogD: 0.03

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -0.39

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