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.

CHEBI:24983 CHEBI:24983
CHEBI:60783 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

Equivalent identifiers for this same structure in other resources.

cas:3258-02-4
chemspider:170635
drugbank:DB15660

Activity roles

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

CHEBI:149553 CHEBI:149553
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: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

Provenance

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