beta-D-2'-deoxy-2'-alpha-fluoro-4'-alpha-cyano-5-aza-7,9-dideaza adenosine

ID: ALA3425971

Chembl Id: CHEMBL3425971

PubChem CID: 56947692

Max Phase: Preclinical

Molecular Formula: C11H13FN4O3

Molecular Weight: 268.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnn2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3F)ccc12

Standard InChI:  InChI=1S/C11H13FN4O3/c12-8-9(18)7(3-17)19-10(8)5-1-2-6-11(13)14-4-15-16(5)6/h1-2,4,7-10,17-18H,3H2,(H2,13,14,15)/t7-,8-,9-,10+/m1/s1

Standard InChI Key:  VFVKYAHCHWXNNT-KYXWUPHJSA-N

Alternative Forms

1. Parent:

   

   ALA3425971

   (2R,3R,4R,5S)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

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: 268.25

Molecular Weight (Monoisotopic): 268.0972

AlogP: -0.56

#Rotatable Bonds: 2

Polar Surface Area: 105.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: 0.78

CX LogP: -0.75

CX LogD: -0.75

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: 0.18

References

1. Clarke MO, Mackman R, Byun D, Hui H, Barauskas O, Birkus G, Chun BK, Doerffler E, Feng J, Karki K, Lee G, Perron M, Siegel D, Swaminathan S, Lee W..  (2015)  Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.,  25  (12): [PMID:25978965] [10.1016/j.bmcl.2015.04.073]

2. Wei D, Hu T, Zhang Y, Zheng W, Xue H, Shen J, Xie Y, Aisa HA..  (2021)  Potency and pharmacokinetics of GS-441524 derivatives against SARS-CoV-2.,  46  [PMID:34450570] [10.1016/j.bmc.2021.116364]

Source

Source(1):

• Scientific Literature