((2R,3R,4R,5S)-5-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate

ID: ALA3287609

Chembl Id: CHEMBL3287609

PubChem CID: 25000921

Max Phase: Preclinical

Molecular Formula: C12H19N4O13P3

Molecular Weight: 520.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(O)[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O[C@H]1c1ccc2c(N)ncnn12

Standard InChI:  InChI=1S/C12H19N4O13P3/c1-12(18)9(17)8(4-26-31(22,23)29-32(24,25)28-30(19,20)21)27-10(12)6-2-3-7-11(13)14-5-15-16(6)7/h2-3,5,8-10,17-18H,4H2,1H3,(H,22,23)(H,24,25)(H2,13,14,15)(H2,19,20,21)/t8-,9-,10+,12-/m1/s1

Standard InChI Key:  WUUJHWINXIGDEU-MWGHHZFTSA-N

Alternative Forms

1. Parent:

   

   ALA3287609

   [[(2R,3R,4R,5S)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

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: 520.22

Molecular Weight (Monoisotopic): 520.0161

AlogP: -0.79

#Rotatable Bonds: 8

Polar Surface Area: 265.72

Molecular Species: ACID

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: 0.49

CX LogP: -2.89

CX LogD: -9.74

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: 0.93

References

1. 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]

2. Kirschberg TA, Metobo S, Clarke MO, Aktoudianakis V, Babusis D, Barauskas O, Birkus G, Butler T, Byun D, Chin G, Doerffler E, Edwards TE, Fenaux M, Lee R, Lew W, Mish MR, Murakami E, Park Y, Squires NH, Tirunagari N, Wang T, Whitcomb M, Xu J, Yang H, Ye H, Zhang L, Appleby TC, Feng JY, Ray AS, Cho A, Kim CU..  (2017)  Discovery of a 2'-fluoro-2'-C-methyl C-nucleotide HCV polymerase inhibitor and a phosphoramidate prodrug with favorable properties.,  27  (8): [PMID:28274633] [10.1016/j.bmcl.2017.02.037]

Source

Source(1):

• Scientific Literature