[2-(6-Amino-8-bromo-purin-9-yl)-ethoxymethyl]-phosphonic acid

ID: ALA66356

Chembl Id: CHEMBL66356

Cas Number: 118552-93-5

PubChem CID: 472192

Max Phase: Preclinical

Molecular Formula: C8H11BrN5O4P

Molecular Weight: 352.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1nc(Br)n2CCOCP(=O)(O)O

Standard InChI:  InChI=1S/C8H11BrN5O4P/c9-8-13-5-6(10)11-3-12-7(5)14(8)1-2-18-4-19(15,16)17/h3H,1-2,4H2,(H2,10,11,12)(H2,15,16,17)

Standard InChI Key:  OQEILKBTUXZPBJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA66356

   Phosphonic acid, [[2-(6-amino-8-bromo-9H-purin-9-yl)ethoxy]methyl]-

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: 352.09

Molecular Weight (Monoisotopic): 350.9732

AlogP: 0.32

#Rotatable Bonds: 5

Polar Surface Area: 136.38

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.33

CX Basic pKa: 2.73

CX LogP: -1.84

CX LogD: -2.78

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.40

Np Likeness Score: -0.69

References

1. Holý A, Günter J, Dvoráková H, Masojídková M, Andrei G, Snoeck R, Balzarini J, De Clercq E..  (1999)  Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base.,  42  (12): [PMID:10377214] [10.1021/jm9811256]

Source

Source(1):

• Scientific Literature