ribavirin 5'-monophosphate (CHEBI:45490)

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CHEBI:45490 - ribavirin 5'-monophosphate

ChEBI ID	CHEBI:45490
ChEBI Name	ribavirin 5'-monophosphate
Stars
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.
Last Modified	27 January 2022
Downloads	Molfile

Formula	C8H13N4O8P
Net Charge	0
Average Mass	324.186
Monoisotopic Mass	324.04710
SMILES	NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)n1
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

Species of Metabolite	Component	Source	Comments
Homo sapiens (ncbitaxon:9606)	blood (UBERON:0000178)	PubMed (25971261)	Found in red blood cells.
Simiiformes (ncbitaxon:314293)	blood (UBERON:0000178)	PubMed (17029670)	Found in monkey red blood cells.

Roles Classification

Biological Roles:

drug metabolite

antiviral agent A substance that destroys or inhibits replication of viruses.

human blood serum metabolite Any metabolite (endogenous or exogenous) found in human blood serum samples.

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 Relation(s)
	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 Relation(s)
Incoming Relation(s)	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

Synonyms	Source
ICN 3847	ChemIDplus
RBV-MP	ChEBI
ribavirin-5'-phosphate	ChemIDplus
ribavirin monophosphate	ChemIDplus
ribavirin-MP	ChEBI
RMP	ChEBI

Manual Xrefs	Databases
90600	ChemSpider
DB14663	DrugBank
HMDB0257208	HMDB
RVP	PDBeChem

Registry Numbers	Sources
CAS:40925-28-8	ChemIDplus

Citations