[3-(4-Amino-2-oxo-2H-pyrimidin-1-yloxy)-4-hydroxy-but-1-enyl]-phosphonic acid

ID: ALA25974

Chembl Id: CHEMBL25974

PubChem CID: 6474395

Max Phase: Preclinical

Molecular Formula: C8H12N3O6P

Molecular Weight: 277.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn(OC(/C=C/P(=O)(O)O)CO)c(=O)n1

Standard InChI:  InChI=1S/C8H12N3O6P/c9-7-1-3-11(8(13)10-7)17-6(5-12)2-4-18(14,15)16/h1-4,6,12H,5H2,(H2,9,10,13)(H2,14,15,16)/b4-2+

Standard InChI Key:  PKUOVKZBNUGTFD-DUXPYHPUSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA25974

   disodium;4-amino-1-[(E)-1-hydroxy-4-phosphonatobut-3-en-2-yl]oxypyrimidin-2-one

2. Parent:

   

   ALA25974

   [(E)-3-(4-amino-2-oxo-pyrimidin-1-yl)oxy-4-hydroxy-but-1-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: 277.17

Molecular Weight (Monoisotopic): 277.0464

AlogP: -1.69

#Rotatable Bonds: 5

Polar Surface Area: 147.90

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: ┄

CX LogP: -1.89

CX LogD: -4.21

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.47

Np Likeness Score: 0.81

References

1. Harnden MR, Parkin A, Parratt MJ, Perkins RM..  (1993)  Novel acyclonucleotides: synthesis and antiviral activity of alkenylphosphonic acid derivatives of purines and a pyrimidine.,  36  (10): [PMID:8496903] [10.1021/jm00062a006]

Source

Source(1):

• Scientific Literature