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

ID: ALA220822

Cas Number: 936095-51-1

PubChem CID: 16124969

Max Phase: Preclinical

Molecular Formula: C14H13Br2N3O6S

Molecular Weight: 511.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(C[C@H](N)C(=O)O)c(=O)n(Cc2c(C(=O)O)sc(Br)c2Br)c1=O

Standard InChI:  InChI=1S/C14H13Br2N3O6S/c1-5-2-18(4-7(17)12(21)22)14(25)19(11(5)20)3-6-8(15)10(16)26-9(6)13(23)24/h2,7H,3-4,17H2,1H3,(H,21,22)(H,23,24)/t7-/m0/s1

Standard InChI Key:  VDFYFXPYXBDMBE-ZETCQYMHSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.7236   -2.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -1.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742   -2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291   -2.8934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -2.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -3.5608    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0090   -2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937   -1.8538    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -0.3863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -1.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    0.8512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873    0.8512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873    1.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    2.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    1.6762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    2.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    3.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873    3.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  6
 24 25  2  0
 24 22  1  0
 21 22  1  0
 24 26  1  0
  2  1  2  0
 15 16  1  0
 13 14  2  0
 15 13  1  0
 15 17  2  0
 13 12  1  0
 17 20  1  0
 11 12  1  0
 11 10  1  0
 18 12  1  0
  2  3  1  0
  4  2  1  0
 18 20  1  0
 21 20  1  0
 18 19  2  0
 10  4  2  0
 10  8  1  0
  4  5  1  0
  9  8  1  0
  8  6  2  0
  6  5  1  0
  7  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA220822

   3-({3-[(2s)-2-Amino-2-Carboxyethyl]-5-Methyl-2,6-Dioxo-3,6-Dihydropyrimidin-1(2h)-Yl}methyl)-4,5-Dibromothiophene-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: 511.15

Molecular Weight (Monoisotopic): 508.8892

AlogP: 1.06

#Rotatable Bonds: 6

Polar Surface Area: 144.62

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: 8.48

CX LogP: -0.45

CX LogD: -3.77

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -0.52

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