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NHC-triphosphate
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| Category | Hepatitis C Virus (HCV) |
| CAS | 34973-27-8 |
| Description | N 4-Hydroxycytidine (NHC) is an antiviral ribonucleoside analog that acts as a competitive alternative substrate for virally encoded RNA-dependent RNA polymerases. NHC-triphosphate is a weak alternative substrate for the viral polymerase and can be incorporated into HCV replicon RNA. |
Product Information
| Synonyms | N4-Hydroxycytidine 5'-triphosphate; N4-hydroxy-CTP; Uridine 5'-(tetrahydrogen triphosphate), 4-oxime; Uridine, 4-oxime, 5'-triphosphate; 1-β-D-Ribofuranosyl-4-hydroxylamino-2-pyrimidinone 5'-triphosphate; EIDD 2061; EIDD-1931 triphosphate; N4-Hydroxycytidine triphosphate |
| IUPAC Name | [[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate |
| Molecular Weight | 499.16 |
| Molecular Formula | C9H16N3O15P3 |
| Canonical SMILES | C1=CN(C(=O)N=C1NO)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O |
| InChI | InChI=1S/C9H16N3O15P3/c13-6-4(3-24-29(20,21)27-30(22,23)26-28(17,18)19)25-8(7(6)14)12-2-1-5(11-16)10-9(12)15/h1-2,4,6-8,13-14,16H,3H2,(H,20,21)(H,22,23)(H,10,11,15)(H2,17,18,19)/t4-,6-,7-,8-/m1/s1 |
| InChIKey | BNIQIYMICUFERK-XVFCMESISA-N |
| Purity | 98% |
| Density | 2.52±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
| Appearance | White or off-white solid |
| Storage | Store at -20°C |
| Complexity | 871 |
| Exact Mass | 498.97942781 |
| In Vitro | In an intracellular metabolism assay, HCV replicon cells are treated with 10 μM 3H-labeled NHC, and intracellular nucleotide levels are determined after 1, 2 and 8 hours incubations. NHC is rapidly convered into the mono-, di-, and triphosphate forms, and NHC-TP reaches up to 71.12 pM after 8 hours. NHC-triphosphate (NHC-TP) (5-40 μM) absence leads to full-length polymerization products, it can be a weak alternative substrate. In addition, incorporation of NHC-TP instead of CTP increases the molecular weight of the polymerization product by 16 (one extra oxygen) for each event and an obvious electrophoretic shift is observed in cell-free HCV NS5B polymerization reactions. Huh-7 cells are incubated with (10-50 μM; 4 h) NHC or a McGuigan phosphoramidate prodrug of NHC. Intracellular levels of the parental compounds and phosphorylated metabolites are measured using LC-MS/MS. Small amounts of NHC- monophosphate (MP) and NHC-diphosphate (DP) can be observed, while NHC-triphosphate (HY-135867) remains the most abundant metabolite. NHC-triphosphate (NHC-TP) metabolite may directly target the viral polymerase and behave as a nonobligate chain terminator. It plays a prominent role in inhibiting early negative-strand RNA synthesis, either through chain termination or mutagenesis, which may in turn interfere with correct replicase complex formation. |
| PSA | 306.09000 |
| Target | IC50: alternative substrate for the viral polymerase |
| XLogP3-AA | -5.7 |
