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

ID: ALA222521

PubChem CID: 16124897

Max Phase: Preclinical

Molecular Formula: C16H17N3O6

Molecular Weight: 347.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(C[C@H](N)C(=O)O)c(=O)n(Cc2ccccc2C(=O)O)c1=O

Standard InChI:  InChI=1S/C16H17N3O6/c1-9-6-18(8-12(17)15(23)24)16(25)19(13(9)20)7-10-4-2-3-5-11(10)14(21)22/h2-6,12H,7-8,17H2,1H3,(H,21,22)(H,23,24)/t12-/m0/s1

Standard InChI Key:  INFYMHSPYPIMBU-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
    4.1066  -10.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054  -11.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203  -11.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5366  -11.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5337  -10.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -9.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8155   -9.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287   -8.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998   -8.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3921   -9.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6778  -10.3204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631   -9.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508  -10.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2468  -11.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9612  -11.5562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796  -11.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642   -9.0823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3936  -11.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586  -12.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2428  -12.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297  -12.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412  -13.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256  -14.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544  -14.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379   -9.9014    0.0000 C   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:

   

   ALA222521

   (S)-1-(2-amino-2-carboxyethyl)-3-(2-carboxybenzyl)-5-methylpyrimidine-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: 347.33

Molecular Weight (Monoisotopic): 347.1117

AlogP: -0.52

#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: 1.65

CX Basic pKa: 8.48

CX LogP: -2.08

CX LogD: -5.29

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: -0.51

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