ribavirin 5'-monophosphate (CHEBI:45490)

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ChEBI Name	ribavirin 5'-monophosphate

ChEBI ID	CHEBI:45490

Definition	A 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a phosphonooxy group. It is the active metabolite of the antiviral agent ribavirin.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C8H13N4O8P

Net Charge

Average Mass

324.186

Monoisotopic Mass

324.04710

InChI

InChI=1S/C8H13N4O8P/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(20-8)1-19-21(16,17)18/h2-5,8,13-14H,1H2,(H2,9,15)(H2,16,17,18)/t3-,4-,5-,8-/m1/s1

InChIKey

SDWIOXKHTFOULX-AFCXAGJDSA-N

SMILES

NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

Metabolite of Species	Details
Simiiformes (NCBI:txid314293)	Found in blood (UBERON:0000178). Found in monkey red blood cells. See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). Found in red blood cells. See: PubMed

Roles Classification
Biological Role(s):	human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples. drug metabolite antiviral agent A substance that destroys or inhibits replication of viruses. EC 1.1.1.205 (IMP dehydrogenase) inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of IMP dehydrogenase (EC 1.1.1.205), so blocking de novo biosynthesis of purine nucleotides.

ChEBI Ontology
Outgoing	ribavirin 5'-monophosphate (CHEBI:45490) has functional parent ribavirin (CHEBI:63580) ribavirin 5'-monophosphate (CHEBI:45490) has role antiviral agent (CHEBI:22587) ribavirin 5'-monophosphate (CHEBI:45490) has role drug metabolite (CHEBI:49103) ribavirin 5'-monophosphate (CHEBI:45490) has role EC 1.1.1.205 (IMP dehydrogenase) inhibitor (CHEBI:53746) ribavirin 5'-monophosphate (CHEBI:45490) has role human blood serum metabolite (CHEBI:85234) ribavirin 5'-monophosphate (CHEBI:45490) is a 1-ribosyltriazole (CHEBI:63594) ribavirin 5'-monophosphate (CHEBI:45490) is a aromatic amide (CHEBI:62733) ribavirin 5'-monophosphate (CHEBI:45490) is a monocarboxylic acid amide (CHEBI:29347) ribavirin 5'-monophosphate (CHEBI:45490) is a primary carboxamide (CHEBI:140324) ribavirin 5'-monophosphate (CHEBI:45490) is a ribose monophosphate (CHEBI:35159) ribavirin 5'-monophosphate (CHEBI:45490) is conjugate acid of ribavirin 5'-monophosphate(2−) (CHEBI:189091)

Incoming	ribavirin 5'-monophosphate(2−) (CHEBI:189091) is conjugate base of ribavirin 5'-monophosphate (CHEBI:45490)

IUPAC Name

1-(5-O-phosphono-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide

Registry Number	Type	Source
40925-28-8	CAS Registry Number	ChemIDplus

Last Modified

27 January 2022