(S)-1-(2-amino-2-carboxyethyl)-5-bromo-3-(2-carboxythiophene-3-yl-methyl)pyrimidine-2,4-dione

ID: ALA221321

PubChem CID: 16124964

Max Phase: Preclinical

Molecular Formula: C13H12BrN3O6S

Molecular Weight: 418.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](Cn1cc(Br)c(=O)n(Cc2ccsc2C(=O)O)c1=O)C(=O)O

Standard InChI:  InChI=1S/C13H12BrN3O6S/c14-7-4-16(5-8(15)11(19)20)13(23)17(10(7)18)3-6-1-2-24-9(6)12(21)22/h1-2,4,8H,3,5,15H2,(H,19,20)(H,21,22)/t8-/m0/s1

Standard InChI Key:  KKTBJRLDYITGOV-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.8028    2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    1.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    0.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    0.3312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6759   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    0.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232    0.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7614    0.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    1.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -0.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9794   -1.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184   -1.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2468   -2.1319    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -0.2630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307    0.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    1.3510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1153    1.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    1.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7284    0.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  7  6  2  0
  4  5  1  0
  8  7  1  0
  8  4  2  0
  9  8  1  0
  4  2  1  0
 19 18  1  0
 19 20  1  0
 17 18  1  0
 15 17  2  0
 11 18  1  0
 16 15  1  0
 15 13  1  0
 11 12  2  0
 11 10  1  0
 13 10  1  0
 13 14  2  0
  9 10  1  0
 22 24  2  0
  2  3  2  0
  2  1  1  0
 22 20  1  0
 22 23  1  0
 20 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA221321

   3-({3-[(2s)-2-Amino-2-Carboxyethyl]-5-Bromo-2,6-Dioxo-3,6-Dihydropyrimidin-1(2h)-Yl}methyl)thiophene-2-Carboxylic Acid

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: 418.23

Molecular Weight (Monoisotopic): 416.9630

AlogP: -0.01

#Rotatable Bonds: 6

Polar Surface Area: 144.62

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 8.48

CX LogP: -1.74

CX LogD: -5.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.60

Np Likeness Score: -0.89

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