[2-(2,6-Diamino-5-methyl-pyrimidin-4-yloxy)-ethoxymethyl]-phosphonic acid

ID: ALA342983

Chembl Id: CHEMBL342983

PubChem CID: 3011374

Max Phase: Preclinical

Molecular Formula: C8H15N4O5P

Molecular Weight: 278.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(N)nc(N)nc1OCCOCP(=O)(O)O

Standard InChI:  InChI=1S/C8H15N4O5P/c1-5-6(9)11-8(10)12-7(5)17-3-2-16-4-18(13,14)15/h2-4H2,1H3,(H2,13,14,15)(H4,9,10,11,12)

Standard InChI Key:  JSPYZDUIKDWUQG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA342983

   2-(2,6-Diamino-5-methyl-pyrimidin-4-yl)oxyethoxymethylphosphonic 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: 278.20

Molecular Weight (Monoisotopic): 278.0780

AlogP: -0.52

#Rotatable Bonds: 6

Polar Surface Area: 153.81

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.31

CX Basic pKa: 7.63

CX LogP: -3.75

CX LogD: -3.51

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.40

Np Likeness Score: -0.44

References

1. Hocková D, Holý A, Masojídková M, Andrei G, Snoeck R, De Clercq E, Balzarini J..  (2003)  5-Substituted-2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidines-acyclic nucleoside phosphonate analogues with antiviral activity.,  46  (23): [PMID:14584956] [10.1021/jm030932o]

2. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

3. Luo M, Groaz E, Snoeck R, Andrei G, Herdewijn P..  (2020)  Amidate Prodrugs of O-2-Alkylated Pyrimidine Acyclic Nucleosides Display Potent Anti-Herpesvirus Activity.,  11  (7): [PMID:32676147] [10.1021/acsmedchemlett.0c00090]

Source

Source(1):

• Scientific Literature