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

ID: ALA1650758

PubChem CID: 50925436

Max Phase: Preclinical

Molecular Formula: C9H13N2O5P

Molecular Weight: 260.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(C/C=C/CP(=O)(O)O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C9H13N2O5P/c1-7-6-11(9(13)10-8(7)12)4-2-3-5-17(14,15)16/h2-3,6H,4-5H2,1H3,(H,10,12,13)(H2,14,15,16)/b3-2+

Standard InChI Key:  YKUCVYAJEHGNTI-NSCUHMNNSA-N

Molfile:  

     RDKit          2D

 17 17  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
   10.4594   -4.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3  4  1  0
  2 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650758

   [(E)-4-(5-methyl-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: 260.19

Molecular Weight (Monoisotopic): 260.0562

AlogP: -0.42

#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: -0.82

CX LogD: -3.18

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.50

Np Likeness Score: -0.26

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