ID: ALA2031678

Max Phase: Preclinical

Molecular Formula: C12H16N4O4

Molecular Weight: 280.28

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1c1ccc2c(N)ncnn12

Standard InChI:  InChI=1S/C12H16N4O4/c1-12(19)9(18)8(4-17)20-10(12)6-2-3-7-11(13)14-5-15-16(6)7/h2-3,5,8-10,17-19H,4H2,1H3,(H2,13,14,15)/t8-,9-,10+,12-/m1/s1

Standard InChI Key:  RLGAXHNBEXKRIZ-MWGHHZFTSA-N

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

Properties

Molecular Weight: 280.28

Molecular Weight (Monoisotopic): 280.1172

AlogP: -1.14

#Rotatable Bonds: 2

Polar Surface Area: 126.13

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.58

CX Basic pKa: 0.78

CX LogP: -1.36

CX LogD: -1.36

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.55

Np Likeness Score: 0.74

References

1. Cho A, Zhang L, Xu J, Babusis D, Butler T, Lee R, Saunders OL, Wang T, Parrish J, Perry J, Feng JY, Ray AS, Kim CU..  (2012)  Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.,  22  (12): [PMID:22578461] [10.1016/j.bmcl.2012.04.065]

2. Cho A, Zhang L, Xu J, Lee R, Butler T, Metobo S, Aktoudianakis V, Lew W, Ye H, Clarke M, Doerffler E, Byun D, Wang T, Babusis D, Carey AC, German P, Sauer D, Zhong W, Rossi S, Fenaux M, McHutchison JG, Perry J, Feng J, Ray AS, Kim CU..  (2014)  Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients.,  57  (5): [PMID:23547794] [10.1021/jm400201a]

3. Draffan AG, Frey B, Pool B, Gannon C, Tyndall EM, Lilly M, Francom P, Hufton R, Halim R, Jahangiri S, Bond S, Nguyen VT, Jeynes TP, Wirth V, Luttick A, Tilmanis D, Thomas JD, Pryor M, Porter K, Morton CJ, Lin B, Duan J, Kukolj G, Simoneau B, McKercher G, Lagacé L, Amad M, Bethell RC, Tucker SP..  (2014)  Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents.,  5  (6): [PMID:24944743] [10.1021/ml500077j]

4. Draffan AG, Frey B, Fraser BH, Pool B, Gannon C, Tyndall EM, Cianci J, Harding M, Lilly M, Hufton R, Halim R, Jahangiri S, Bond S, Jeynes TP, Nguyen VT, Wirth V, Luttick A, Tilmanis D, Pryor M, Porter K, Morton CJ, Lin B, Duan J, Bethell RC, Kukolj G, Simoneau B, Tucker SP..  (2014)  Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents.,  24  (21): [PMID:25288185] [10.1016/j.bmcl.2014.09.030]

5. Li Q,Groaz E,Rocha-Pereira J,Neyts J,Herdewijn P.  (2020)  Anti-norovirus activity of C7-modified 4-amino-pyrrolo[2,1-f][1,2,4]triazine C-nucleosides.,  195  [PMID:32294613] [10.1016/j.ejmech.2020.112198]

Source

Source(1):

• Scientific Literature