(S)-2,6-Diamino-N6-(2-methoxyethyl)-9-[3-fluoro-2-(phosphonomethoxy)propyl]purine

ID: ALA1766274

Chembl Id: CHEMBL1766274

PubChem CID: 54582472

Max Phase: Preclinical

Molecular Formula: C12H20FN6O5P

Molecular Weight: 378.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNc1nc(N)nc2c1ncn2C[C@@H](CF)OCP(=O)(O)O

Standard InChI:  InChI=1S/C12H20FN6O5P/c1-23-3-2-15-10-9-11(18-12(14)17-10)19(6-16-9)5-8(4-13)24-7-25(20,21)22/h6,8H,2-5,7H2,1H3,(H2,20,21,22)(H3,14,15,17,18)/t8-/m1/s1

Standard InChI Key:  OUXUULYMVFKSDW-MRVPVSSYSA-N

Alternative Forms

1. Parent:

   

   ALA1766274

   [(2S)-1-[2-amino-6-(2-methoxyethylamino)purin-9-yl]-3-fluoropropan-2-yl]oxymethylphosphonic 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: 378.30

Molecular Weight (Monoisotopic): 378.1217

AlogP: -0.04

#Rotatable Bonds: 10

Polar Surface Area: 157.64

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -5.45

CX Basic pKa: 6.37

CX LogP: -4.14

CX LogD: -3.62

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.33

Np Likeness Score: -0.77

References

1. Baszczyňski O, Jansa P, Dračínský M, Klepetářová B, Holý A, Votruba I, de Clercq E, Balzarini J, Janeba Z..  (2011)  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.,  19  (7): [PMID:21429755] [10.1016/j.bmc.2011.02.050]

Source

Source(1):

• Scientific Literature