ribavirin 5'-monophosphate
CHEBI:45490
·resolve ·ANTIVIRAL
·EXACT
REVIEWED
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. — ChEBI
Classification
Strictly broader compounds or drug classes this molecule belongs to.
Chemical structure
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
Also called
- 1-(5-O-phosphono-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide (EXACT_SYNONYM)— chebi
- ICN 3847 (EXACT_SYNONYM)— chebi
- RBV-MP (EXACT_SYNONYM)— chebi
- RMP (EXACT_SYNONYM)— chebi
- ribavirin monophosphate (EXACT_SYNONYM)— chebi
- ribavirin-5'-phosphate (EXACT_SYNONYM)— chebi
- ribavirin-MP (EXACT_SYNONYM)— chebi
- virazole 5'-phosphate (EXACT_SYNONYM)— chebi
Cross-references
Identifiers for this same structure in other resources. An
accession that lands on two different structures in this corpus is withheld from
both rather than shown here, since it names at most one of them.
Drug registries
Identifiers that name a drug rather than a structure. One of
these can cover a parent compound, its salts and its stereoisomers, which this
corpus keeps as separate records, so it is not an equivalence of structure.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
Source concepts
Every upstream concept that resolved to this record. The merge is
the product: this is what shows ChEBI and CARD are describing the same structure.
Molecular targets
The molecular entity or process this compound acts on. Each target
carries evidence — this is a mechanistic claim, not a classification.
inosine monophosphate dehydrogenase (IMPDH) PROTEIN DIRECT_BINDING_TARGET
High-resolution cocrystals of T. foetus IMPDH contained ribavirin 5'-monophosphate alone and with mycophenolic acid, defining the inhibitor-bound active-site architecture. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2002-09 (retrieved 2026-09-02).
- PMID:12235158 (Primary ribavirin-monophosphate-bound protozoan IMPDH structure (DOI:10.1074/jbc.M208330200).)
Mechanism summary
- Mode of action
- NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:12235158 resolved ribavirin 5'-monophosphate bound to Tritrichomonas foetus IMP dehydrogenase. IMPDH catalyzes the rate-limiting step in GMP biosynthesis; its inhibition depletes guanine nucleotides needed for RNA and DNA synthesis. IMPDH is conserved across microbial and host cells, with isoform-dependent inhibitor sensitivity.
Record-level evidence
- PMID:12235158 (Primary exact-metabolite IMPDH cocrystal and GMP-biosynthesis mechanism study.)
Curation history
-
SEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
-
REVIEWED
2026-09-02 · codex · LLM-assisted
Verified exact ChEBI metabolite identity, structure, antiviral role, and class; added guanine-nucleotide synthesis inhibition and the directly bound protozoan IMPDH target with host-shared scope.
-
RESEEDED_FROM_SOURCES
2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
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