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> Main
CHEBI:180654 -
N
4
-hydroxycytidine
Main
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ChEBI Name
N
4
-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
N
4
-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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Molfile
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Molfile
Formula
C9H13N3O6
Net Charge
0
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
N
4
-hydroxycytidine (
CHEBI:180654
)
has functional parent
cytidine (
CHEBI:17562
)
N
4
-hydroxycytidine (
CHEBI:180654
)
has role
anticoronaviral agent (
CHEBI:149553
)
N
4
-hydroxycytidine (
CHEBI:180654
)
has role
antiviral agent (
CHEBI:22587
)
N
4
-hydroxycytidine (
CHEBI:180654
)
has role
drug metabolite (
CHEBI:49103
)
N
4
-hydroxycytidine (
CHEBI:180654
)
has role
human xenobiotic metabolite (
CHEBI:76967
)
N
4
-hydroxycytidine (
CHEBI:180654
)
is a
ketoxime (
CHEBI:24983
)
N
4
-hydroxycytidine (
CHEBI:180654
)
is a
nucleoside analogue (
CHEBI:60783
)
Incoming
molnupiravir (
CHEBI:180653
)
has functional parent
N
4
-hydroxycytidine (
CHEBI:180654
)
IUPAC Name
N
-hydroxy-3,4-dihydrocytidine
Synonyms
Sources
1-
[(2
R
,3
R
,4
S
,5
R
)-
3,4-
dihydroxy-
5-
(hydroxymethyl)tetrahydrofuran-
2-
yl]-
4-
(hydroxyimino)-
3,4-
dihydropyrimidin-
2(1
H
)-
one
IUPAC
4-
N
-hydroxycytidine
ChemIDplus
4-oxime uridine
ChemIDplus
β-
D
-
N
4
-hydroxycytidine
DrugBank
EIDD 1931
ChEBI
EIDD-1931
DrugBank
N
(4)-hydroxycytidine
ChemIDplus
N
-hydroxycytidine
ChemIDplus
NHC
DrugBank
Manual Xrefs
Databases
170635
ChemSpider
DB15660
DrugBank
View more database links
Registry Number
Type
Source
3258-02-4
CAS Registry Number
ChemIDplus
Citations
Types
Sources
31494195
PubMed citation
Europe PMC
31578288
PubMed citation
Europe PMC
31645453
PubMed citation
Europe PMC
32253226
PubMed citation
Europe PMC
33290476
PubMed citation
Europe PMC
33327924
PubMed citation
Europe PMC
33649113
PubMed citation
Europe PMC
33807492
PubMed citation
Europe PMC
33989635
PubMed citation
Europe PMC
34186107
PubMed citation
Europe PMC
34357881
PubMed citation
Europe PMC
34381216
PubMed citation
Europe PMC
34503974
PubMed citation
Europe PMC
34509661
PubMed citation
Europe PMC
Last Modified
01 October 2021