NHC-diphosphate

Category	Hepatitis C Virus (HCV)
CAS	39023-73-9
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-diphosphate is an active phosphorylated form.

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Synonyms	NHC-diphosphate\|HY-135867D\|CS-0139063
IUPAC Name	[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl phosphono hydrogen phosphate
Molecular Weight	419.18
Molecular Formula	C9H15N3O12P2
Canonical SMILES	C1=CN(C(=O)N=C1NO)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)O)O)O
InChI	InChI=1S/C9H15N3O12P2/c13-6-4(3-22-26(20,21)24-25(17,18)19)23-8(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,10,11,15)(H2,17,18,19)/t4-,6-,7-,8-/m1/s1
InChIKey	LCSZLCQPBIHOHF-XVFCMESISA-N
Purity	98%
Solubility	In vitro: 10 mM in DMSO
Appearance	White to off-white (Solid)
Storage	Store at -20°C
Complexity	706
Exact Mass	419.01309692
In Vitro	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; HY-135867D) can be observed, while NHC-triphosphate remains the most abundant metabolite. Metabolism of the anti-hepatitis C virus nucleoside beta-D-N4-hydroxycytidine in different liver cells.
In Vivo	Huh-7 cells are incubated with (10-50 μM; 4 h) NHC or a McGuigan phosphoramidate prodrug of NHC.
Target	IC50: alternative substrate for the viral polymerase
XLogP3-AA	-4.6