(S)-1-(2-amino-2-carboxyethyl)-3-(2-carboxyfuran-3-yl-methyl)-5-methylpyrimidine-2,4-dione

ID: ALA220509

PubChem CID: 16125157

Max Phase: Preclinical

Molecular Formula: C14H15N3O7

Molecular Weight: 337.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(C[C@H](N)C(=O)O)c(=O)n(Cc2ccoc2C(=O)O)c1=O

Standard InChI:  InChI=1S/C14H15N3O7/c1-7-4-16(6-9(15)12(19)20)14(23)17(11(7)18)5-8-2-3-24-10(8)13(21)22/h2-4,9H,5-6,15H2,1H3,(H,19,20)(H,21,22)/t9-/m0/s1

Standard InChI Key:  FVOROBNPSXTTAH-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 24 25  0  0  1  0  0  0  0  0999 V2000
   13.5548  -22.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8405  -22.9211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1257  -22.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4134  -22.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4094  -23.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1238  -24.1570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8423  -23.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1268  -21.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5563  -24.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1212  -24.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4054  -25.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6922  -24.9774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4038  -26.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6881  -26.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1170  -26.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2694  -22.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3600  -23.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1670  -23.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5794  -23.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0271  -22.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1977  -21.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9833  -21.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5853  -21.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7004  -22.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1
  4  5  2  0
  5  6  1  0
  6  7  1  0
 13 14  1  0
 13 15  2  0
 11 13  1  0
  2  3  1  0
  1 16  1  0
 16 17  1  0
  3  8  2  0
  7  9  2  0
  1  2  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
  6 10  1  0
 20 21  1  0
  2  7  1  0
 10 11  1  0
 21 22  1  0
 21 23  2  0
  3  4  1  0
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA220509

   (S)-1-(2-amino-2-carboxyethyl)-3-(2-carboxyfuran-3-yl-methyl)-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: 337.29

Molecular Weight (Monoisotopic): 337.0910

AlogP: -0.93

#Rotatable Bonds: 6

Polar Surface Area: 157.76

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.88

CX Basic pKa: 8.48

CX LogP: -3.14

CX LogD: -6.40

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.40

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