N4-hydroxycytidine

CHEBI:180654 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A nucleoside analogue that is cytidine which carries a hydroxy group at the N4-positon. It has broad-spectrum antiviral activity against influenza, SARS-CoV , SARS-CoV-2 and MERS-CoV. — 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:24983
Label unavailable CHEBI:60783

Chemical structure

Computed structure properties
Molecular formula	C9H13N3O6
Charge	0
Average mass	259.218 Da
Monoisotopic mass	259.08044 Da
Source	ChEBI
InChIKey	XCUAIINAJCDIPM-XVFCMESISA-N

SMILES

O=c1nc(=NO)ccn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI

InChI=1S/C9H13N3O6/c13-3-4-6(14)7(15)8(18-4)12-2-1-5(11-17)10-9(12)16/h1-2,4,6-8,13-15,17H,3H2,(H,10,11,16)/t4-,6-,7-,8-/m1/s1

Also called

N-hydroxy-3,4-dihydrocytidine (EXACT_SYNONYM)— chebi
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
4-N-hydroxycytidine (EXACT_SYNONYM)— chebi
4-oxime uridine (EXACT_SYNONYM)— chebi
EIDD 1931 (EXACT_SYNONYM)— chebi
EIDD-1931 (EXACT_SYNONYM)— chebi
N(4)-hydroxycytidine (EXACT_SYNONYM)— chebi
N-hydroxycytidine (EXACT_SYNONYM)— chebi
NHC (EXACT_SYNONYM)— chebi
β-D-N4-hydroxycytidine (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.

drugbank:DB15660

Activity roles

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

anticoronaviral agent CHEBI:149553
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:180654`	N4-hydroxycytidine	`antibioticmech:chebi-82bc2fb6e2`	2026-08-30

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 2026-09-10 · 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/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (N4-hydroxycytidine) · CultureMech · NaturalProductMech · PathwayMech · TraitMech