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.

CHEBI:191947 CHEBI:191947
CHEBI:38337 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

Equivalent identifiers for this same structure in other resources.

chemspider:7989048

Activity roles

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

CHEBI:22587 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.