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

ID: ALA298845

Chembl Id: CHEMBL298845

Cas Number: 429676-19-7

PubChem CID: 493045

Max Phase: Preclinical

Molecular Formula: C7H13N4O5P

Molecular Weight: 264.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cc(OCCOCP(=O)(O)O)nc(N)n1

Standard InChI:  InChI=1S/C7H13N4O5P/c8-5-3-6(11-7(9)10-5)16-2-1-15-4-17(12,13)14/h3H,1-2,4H2,(H2,12,13,14)(H4,8,9,10,11)

Standard InChI Key:  GHXCAFKFSYKTJZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA298845

   Phosphonic acid, [[2-[(2,6-diamino-4-pyrimidinyl)oxy]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: 264.18

Molecular Weight (Monoisotopic): 264.0624

AlogP: -0.83

#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: 0.32

CX Basic pKa: 7.71

CX LogP: -4.25

CX LogD: -4.09

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.38

Np Likeness Score: -0.47

References

1. Holý A, Votruba I, Masojídková M, Andrei G, Snoeck R, Naesens L, De Clercq E, Balzarini J..  (2002)  6-[2-(Phosphonomethoxy)alkoxy]pyrimidines with antiviral activity.,  45  (9): [PMID:11960502] [10.1021/jm011095y]

2. 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]

3. Brunelle MN, Lucifora J, Neyts J, Villet S, Holy A, Trepo C, Zoulim F..  (2007)  In vitro activity of 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]-pyrimidine against multidrug-resistant hepatitis B virus mutants.,  51  (6): [PMID:17371827] [10.1128/aac.01440-06]

4. Lebeau I, Andrei G, Krecmerová M, De Clercq E, Holy A, Snoeck R..  (2007)  Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.,  51  (6): [PMID:17420214] [10.1128/aac.01422-06]

5. Duraffour S, Snoeck R, Krecmerová M, van Den Oord J, De Vos R, Holy A, Crance JM, Garin D, De Clercq E, Andrei G..  (2007)  Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.,  51  (12): [PMID:17893157] [10.1128/aac.00838-07]

6. Shi M, Wang X, De Clercq E, Takao S, Baba M..  (2007)  Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.,  51  (7): [PMID:17470654] [10.1128/aac.00212-07]

7. 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]

8. Krečmerová M, Dračínský M, Snoeck R, Balzarini J, Pomeisl K, Andrei G..  (2017)  New prodrugs of two pyrimidine acyclic nucleoside phosphonates: Synthesis and antiviral activity.,  25  (17): [PMID:28757102] [10.1016/j.bmc.2017.06.046]

9. de Castro S, Camarasa MJ..  (2018)  Polypharmacology in HIV inhibition: can a drug with simultaneous action against two relevant targets be an alternative to combination therapy?,  150  [PMID:29529501] [10.1016/j.ejmech.2018.03.007]

Source

Source(1):

• Scientific Literature