(S)-1-(2-amino-2-carboxyethyl)-3-(2-carboxybenzyl)-5-fluoropyrimidine-2,4-dione

ID: ALA223841

PubChem CID: 16125032

Max Phase: Preclinical

Molecular Formula: C15H14FN3O6

Molecular Weight: 351.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](Cn1cc(F)c(=O)n(Cc2ccccc2C(=O)O)c1=O)C(=O)O

Standard InChI:  InChI=1S/C15H14FN3O6/c16-10-6-18(7-11(17)14(23)24)15(25)19(12(10)20)5-8-3-1-2-4-9(8)13(21)22/h1-4,6,11H,5,7,17H2,(H,21,22)(H,23,24)/t11-/m0/s1

Standard InChI Key:  IGJMSGMPZLVKKS-NSHDSACASA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
   10.0755  -10.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0744  -11.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7890  -11.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5053  -11.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5025  -10.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7872   -9.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7843   -9.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4974   -8.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0688   -8.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3611   -9.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6469  -10.2813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9322   -9.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2202  -10.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2161  -11.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9303  -11.5170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6487  -11.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9333   -9.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625  -11.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277  -12.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2121  -12.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992  -12.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2106  -13.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4950  -13.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9235  -13.9924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5074   -9.8624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  2  0
  3  4  2  0
 11 16  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
  7  8  1  0
 12 17  2  0
  7  9  2  0
 16 18  2  0
  6  7  1  0
 15 19  1  0
  4  5  1  0
 19 20  1  0
  1 10  1  0
 20 21  1  1
  2  3  1  0
 10 11  1  0
 11 12  1  0
 22 23  1  0
 22 24  2  0
 20 22  1  0
  5  6  2  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA223841

   (S)-1-(2-amino-2-carboxyethyl)-3-(2-carboxybenzyl)-5-fluoropyrimidine-2,4-dione

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: 351.29

Molecular Weight (Monoisotopic): 351.0867

AlogP: -0.69

#Rotatable Bonds: 6

Polar Surface Area: 144.62

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.67

CX Basic pKa: 8.48

CX LogP: -2.27

CX LogD: -5.49

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.71

References

1. Dolman NP, More JC, Alt A, Knauss JL, Pentikäinen OT, Glasser CR, Bleakman D, Mayer ML, Collingridge GL, Jane DE..  (2007)  Synthesis and pharmacological characterization of N3-substituted willardiine derivatives: role of the substituent at the 5-position of the uracil ring in the development of highly potent and selective GLUK5 kainate receptor antagonists.,  50  (7): [PMID:17348638] [10.1021/jm061041u]

Source

Source(1):

• Scientific Literature