N1-[(E)-5-Dihydroxyphosphonyl-pent-2-enyl]-thymine

ID: ALA1650762

PubChem CID: 15986886

Max Phase: Preclinical

Molecular Formula: C10H15N2O5P

Molecular Weight: 274.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H15N2O5P/c1-8-7-12(10(14)11-9(8)13)5-3-2-4-6-18(15,16)17/h2-3,7H,4-6H2,1H3,(H,11,13,14)(H2,15,16,17)/b3-2+

Standard InChI Key:  OPTUJJWAHBAMIG-NSCUHMNNSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.4282  -13.1483    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2776  -10.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2776  -11.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900  -11.9129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019  -11.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7022  -10.6790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900  -10.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900   -9.4371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165  -11.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900  -12.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2754  -13.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610  -12.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500  -13.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392  -12.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173  -12.7377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282  -13.9692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126  -13.5552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620  -10.2686    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 14  1  0
 14  1  1  0
  1 15  1  0
  2  3  2  0
  1 16  2  0
  2  7  1  0
  1 17  1  0
  3  4  1  0
  2 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650762

   [(E)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)pent-3-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: 274.21

Molecular Weight (Monoisotopic): 274.0719

AlogP: -0.03

#Rotatable Bonds: 5

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: 1.81

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -2.90

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.52

Np Likeness Score: 0.02

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