ribavirin 5'-triphosphate

CHEBI:45578 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

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

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140324
Label unavailable CHEBI:26563
Label unavailable CHEBI:29347
Label unavailable CHEBI:62733
Label unavailable CHEBI:63594

Chemical structure

Computed structure properties
Molecular formula	C8H15N4O14P3
Charge	0
Average mass	484.144 Da
Monoisotopic mass	483.97976 Da
Source	ChEBI
InChIKey	MMJOCKKLRMRSEQ-AFCXAGJDSA-N

SMILES

NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)n1

InChI

InChI=1S/C8H15N4O14P3/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(24-8)1-23-28(19,20)26-29(21,22)25-27(16,17)18/h2-5,8,13-14H,1H2,(H2,9,15)(H,19,20)(H,21,22)(H2,16,17,18)/t3-,4-,5-,8-/m1/s1

Also called

1-[5-O-(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)-β-D-ribofuranosyl]-1H-1,2,4-triazole-3-carboxamide (EXACT_SYNONYM)— chebi
1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-triphosphate (EXACT_SYNONYM)— chebi
RBV-TP (EXACT_SYNONYM)— chebi
RTP (EXACT_SYNONYM)— chebi
ribavirin triphosphate (EXACT_SYNONYM)— chebi
ribavirin-TP (EXACT_SYNONYM)— chebi
virazole 5'-triphosphate (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.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral agent CHEBI:22587

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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:45578`	ribavirin 5'-triphosphate	`antibioticmech:chebi-970b487d3b`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

dengue virus NS5 mRNA 2'-O-methyltransferase domain VIRAL_PROTEIN DIRECT_BINDING_TARGET

Enzyme assays showed competitive inhibition with GTP, and a 2.6-angstrom ternary cocrystal directly located ribavirin 5'-triphosphate in the viral NS5 methyltransferase domain. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2004-05 (retrieved 2026-09-02).

PMID:15152003 (Primary enzyme-inhibition and ternary-cocrystal study (DOI:10.1074/jbc.m400460200).)

hepatitis C virus NTPase/helicase VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Biochemical unwinding kinetics measured a reduced helicase turnover number; the inspected report did not establish a compound-bound structure. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2001 (retrieved 2026-09-02).

PMID:11833782 (Primary HCV helicase unwinding-kinetics study.)

hepatitis C virus RNA-dependent RNA polymerase VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

In-vitro initiation and elongation assays compared ribavirin triphosphate and ribose-modified analogues against HCV RNA polymerase; no compound-polymerase cocrystal was reported. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2003-03 (retrieved 2026-09-02).

PMID:12606760 (Primary HCV polymerase initiation/elongation and analogue-activation study.)

Mechanism summary

Mode of action: MULTIPLE microbial target — CURATOR: the exact triphosphate has more than one experimentally supported viral-enzyme interaction. PMID:15152003 directly structures competitive binding to dengue NS5 2'-O-methyltransferase; PMID:11833782 measures inhibition of HCV NTPase/helicase; and PMID:12606760 tests ribavirin nucleotides against HCV polymerase. The prior polymerase-only seed was therefore too narrow. Published eIF4E results conflict and are kept as an open controversy rather than asserted as a target.

Discussions

Open questions, knowledge gaps and curation todos attached to this compound.

CONTROVERSY OPEN

Does ribavirin 5'-triphosphate bind eIF4E with physiologically relevant affinity and inhibit cap-dependent translation?

PMID:16131589 reported weak binding and no eIF4E-specific translation inhibition in vitro, whereas PMID:23583375 reported concentration-dependent NMR evidence for a higher-affinity complex. Resolving the assay-dependent discrepancy would determine whether a host target belongs in the curated mechanism.

Attached to: mode_of_action, molecular_targets

Record-level evidence

PMID:15152003 (Primary dengue NS5 methyltransferase cocrystal study.)
PMID:11833782 (Primary HCV helicase kinetics study.)
PMID:12606760 (Primary HCV polymerase and activation 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 identity, structure, and antiviral class; corrected the polymerase-only mechanism to MULTIPLE, added three viral-enzyme targets with primary evidence, and documented the unresolved eIF4E binding controversy without asserting it as fact.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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