N(4)-hydroxycytidine (CHEBI:180654)

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ChEBI Name	N⁴-hydroxycytidine

ChEBI ID	CHEBI:180654

ChEBI ASCII Name	N(4)-hydroxycytidine

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C9H13N3O6

Net Charge

Average Mass

259.218

Monoisotopic Mass

259.08044

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

InChIKey

XCUAIINAJCDIPM-XVFCMESISA-N

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(NC1=O)=NO

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in saliva (UBERON:0001836). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood plasma (BTO:0000118). See: PubMed

Roles Classification
Biological Role(s):	drug metabolite human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. antiviral agent A substance that destroys or inhibits replication of viruses.

ChEBI Ontology
Outgoing	N⁴-hydroxycytidine (CHEBI:180654) has functional parent cytidine (CHEBI:17562) N⁴-hydroxycytidine (CHEBI:180654) has role anticoronaviral agent (CHEBI:149553) N⁴-hydroxycytidine (CHEBI:180654) has role antiviral agent (CHEBI:22587) N⁴-hydroxycytidine (CHEBI:180654) has role drug metabolite (CHEBI:49103) N⁴-hydroxycytidine (CHEBI:180654) has role human xenobiotic metabolite (CHEBI:76967) N⁴-hydroxycytidine (CHEBI:180654) is a ketoxime (CHEBI:24983) N⁴-hydroxycytidine (CHEBI:180654) is a nucleoside analogue (CHEBI:60783)

Incoming	molnupiravir (CHEBI:180653) has functional parent N⁴-hydroxycytidine (CHEBI:180654)

IUPAC Name

N-hydroxy-3,4-dihydrocytidine

Synonyms	Sources
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1H)-one	IUPAC
4-N-hydroxycytidine	ChemIDplus
4-oxime uridine	ChemIDplus
β-D-N⁴-hydroxycytidine	DrugBank
EIDD 1931	ChEBI
EIDD-1931	DrugBank
N(4)-hydroxycytidine	ChemIDplus
N-hydroxycytidine	ChemIDplus
NHC	DrugBank

Registry Number	Type	Source
3258-02-4	CAS Registry Number	ChemIDplus

Last Modified

01 October 2021