3'-deoxy-3',4'-didehydro-cytidine

CHEBI:156331 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyrimidine 3'-deoxyribonucleoside that is cytidine in which the hydroxy group at position 3' is replaced by a hydrogen and a double bond is introduced between positions 3' and 4'. It is a metabolite of 3'-deoxy-3',4'-didehydro-CTP. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:191947
Label unavailable CHEBI:38337

Chemical structure

Computed structure properties
Molecular formula	C9H11N3O4
Charge	0
Average mass	225.204 Da
Monoisotopic mass	225.07496 Da
Source	ChEBI
InChIKey	VQMYKNBUURJYAP-HTRCEHHLSA-N

SMILES

Nc1ccn([C@@H]2OC(CO)=C[C@H]2O)c(=O)n1

InChI

InChI=1S/C9H11N3O4/c10-7-1-2-12(9(15)11-7)8-6(14)3-5(4-13)16-8/h1-3,6,8,13-14H,4H2,(H2,10,11,15)/t6-,8-/m1/s1

Also called

4-amino-1-[(2R,3R)-3-hydroxy-5-(hydroxymethyl)-2,3-dihydrofuran-2-yl]pyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
3',4'-didehydro-3'-deoxycytidine (EXACT_SYNONYM)— chebi
4-amino-1-[(2R,3R)-3-hydroxy-5-(hydroxymethyl)-2,3-dihydro-2-furanyl]-2(1H)-pyrimidinone (EXACT_SYNONYM)— chebi
4-amino-1-[(2R,3R)-3-hydroxy-5-(hydroxymethyl)-2,3-dihydrofuran-2-yl]-2-pyrimidinone (EXACT_SYNONYM)— chebi
4-amino-1-[(2R,3R)-3-hydroxy-5-(hydroxymethyl)-2,3-dihydrofuran-2-yl]pyrimidin-2-one (EXACT_SYNONYM)— chebi
4-amino-1-[(2R,3R)-3-hydroxy-5-methylol-2,3-dihydrofuran-2-yl]pyrimidin-2-one (EXACT_SYNONYM)— chebi
ddh-cytidine (EXACT_SYNONYM)— chebi
ddhC (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.

chemspider:7989048

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:156331`	3'-deoxy-3',4'-didehydro-cytidine	`antibioticmech:chebi-41361bfb6b`	2026-08-30

Mechanism summary

Mode of action: MULTIPLE microbial target — Assigned from ChEBI roles CHEBI:170010 (EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor), CHEBI:48001 (protein synthesis inhibitor), which map to PROTEIN_SYNTHESIS_INHIBITION, VIRAL_POLYMERASE_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. The contributing roles differ on whose target it is, so settling the primary mechanism may change mode_of_action_target_scope. Not a curator's mechanistic review.

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
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · 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/. View the record (YAML).

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