N1-[(E)-4-Dihydroxyphosphonyl-but-2-enyl]-uracil

ID: ALA1650754

PubChem CID: 24853892

Max Phase: Preclinical

Molecular Formula: C8H11N2O5P

Molecular Weight: 246.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn(C/C=C/CP(=O)(O)O)c(=O)[nH]1

Standard InChI:  InChI=1S/C8H11N2O5P/c11-7-3-5-10(8(12)9-7)4-1-2-6-16(13,14)15/h1-3,5H,4,6H2,(H,9,11,12)(H2,13,14,15)/b2-1+

Standard InChI Key:  GXKCIWVPHHHYHS-OWOJBTEDSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    9.0301   -6.7454    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.1756   -4.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1756   -5.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8880   -5.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5999   -5.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6006   -4.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8881   -4.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8881   -3.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3143   -5.9255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8880   -6.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1735   -7.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4591   -6.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7446   -7.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0301   -5.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156   -7.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -6.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  5  9  2  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  1  1  0
  1 14  2  0
  2  3  2  0
  1 15  1  0
  2  7  1  0
  1 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650754

   [(E)-4-(2,4-dioxopyrimidin-1-yl)but-2-enyl]phosphonic 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: 246.16

Molecular Weight (Monoisotopic): 246.0406

AlogP: -0.73

#Rotatable Bonds: 4

Polar Surface Area: 112.39

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.74

CX Basic pKa: ┄

CX LogP: -1.16

CX LogD: -3.53

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.48

Np Likeness Score: -0.12

References

1. Topalis D, Pradère U, Roy V, Caillat C, Azzouzi A, Broggi J, Snoeck R, Andrei G, Lin J, Eriksson S, Alexandre JA, El-Amri C, Deville-Bonne D, Meyer P, Balzarini J, Agrofoglio LA..  (2011)  Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.,  54  (1): [PMID:21128666] [10.1021/jm1011462]

Source

Source(1):

• Scientific Literature