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Compound Detail

CHEMBL2178720

N-HYDROXYCYTIDINE
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O=c1nc(NO)ccn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2178720
Name N-HYDROXYCYTIDINE
Phase Preclinical
Structure Type MOL
InChI Key XCUAIINAJCDIPM-XVFCMESISA-N

Known Names

N-hydroxycytidine
8
Targets
20
Activities
1
Assay Types
6
PK Parameters
20
Publications
1
Known Names

Molecular Properties

259.2
MW (Da)
-2.34
ALogP
9
HBA
5
HBD
137.1
PSA (Ų)
0.38
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown
USAN Stem -tidine

Extended Properties

Molecular Formula C9H13N3O6
MW 259.22
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.31

Activity Summary

EC50 20 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Middle East respiratory syndrome-related coronavirus
CHEMBL4296578
 EC50 7.62 6.75 24.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 7.1 6.349 80.0 10
SARS-CoV
CHEMBL4303836
 EC50 6.85 6.33 140.0 2
Chikungunya virus
CHEMBL4296563
 EC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
 EC50 5.92 5.92 1194.0 1
Influenza A virus
CHEMBL613740
 EC50 5.77 5.705 1700.0 2
Venezuelan equine encephalitis virus
CHEMBL613726
 EC50 5.64 5.64 2300.0 1
dengue virus type 2
CHEMBL613966
 EC50 5.55 5.55 2840.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 56.0 % Mus musculus
F 43.0 % Mus musculus
F 36.0 % Mus musculus
T1/2 5.2 hr Mus musculus
T1/2 3.2 hr Mus musculus
T1/2 2.7 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Middle East respiratory syndrome-related coronavirus EC50 = 24.0 nM 7.62 Antiviral activity against MERS CoV clinical isolate 2019-nCoV/USA-WA1/2020 infe... 33186044
SARS-CoV-2 EC50 = 80.0 nM 7.1 Antiviral activity against SARS CoV-2 clinical isolate 2019-nCoV/USA-WA1/2020 in... 33186044
SARS-CoV EC50 = 140.0 nM 6.85 Antiviral activity against SARS CoV clinical isolate 2019-nCoV/USA-WA1/2020 infe... 33186044
SARS-CoV-2 EC50 = 204.0 nM 6.69 Antiviral activity against wild type SARS CoV-2 infected in Vero E6 cells transf... 36229406
SARS-CoV-2 EC50 = 238.0 nM 6.62 Antiviral activity against wild type SARS CoV-2 infected in Vero E6 cells transf... 36229406
SARS-CoV-2 EC50 = 300.0 nM 6.52 Antiviral activity against SARS CoV-2 clinical isolate 2019-nCoV/USA-WA1/2020 in... 33186044
SARS-CoV-2 EC50 = 336.0 nM 6.47 Antiviral activity against SARS CoV-2 omicron TY38-873 BA.2 variant infected in ... 36229406
SARS-CoV-2 EC50 = 351.0 nM 6.46 Antiviral activity against SARS CoV-2 delta TY11-927 infected in HEK293T cells t... 36229406
SARS-CoV-2 EC50 = 446.0 nM 6.35 Antiviral activity against wild type SARS CoV-2 infected in HEK293T cells transf... 36229406
SARS-CoV-2 EC50 = 574.0 nM 6.24 Antiviral activity against SARS CoV-2 omicron TY38-873 BA.1 variant infected in ... 36229406
Chikungunya virus EC50 = 1000.0 nM 6.0 Antiviral activity against CHIKV expressing 181/25-nLuc-capsid infected in human... 39235978
Unchecked EC50 = 1194.0 nM 5.92 Antiviral activity against HCoV-OC43 infected in HEK293T cells transfected with ... 36229406
SARS-CoV-2 EC50 = 1222.0 nM 5.91 Antiviral activity against SARS CoV-2 alpha QK002 infected in HEK293T cells tran... 36229406
Middle East respiratory syndrome-related coronavirus EC50 = 1318.0 nM 5.88 Antiviral activity against MERS-CoV EMC2012 infected in HEK293T cells transfecte... 36229406
SARS-CoV EC50 = 1556.0 nM 5.81 Antiviral activity against SARS CoV infected in HEK293T cells transfected with A... 36229406
Influenza A virus EC50 = 1700.0 nM 5.77 Antiviral activity against Influenza A virus A/Puerto Rico/8/34 (H1N1) infected ... 36764470
Influenza A virus EC50 = 2300.0 nM 5.64 Antiviral activity against Influenza A virus A/Hong Kong/8/68 (H3N2) infected in... 36764470
Venezuelan equine encephalitis virus EC50 = 2300.0 nM 5.64 Antiviral activity against Venezuelan equine encephalitis virus infected in huma... 37591319
dengue virus type 2 EC50 = 2840.0 nM 5.55 Antiviral activity against Dengue virus 2 infected in hamster BHK-21 cells incub... 36764470
SARS-CoV-2 EC50 = 7400.0 nM 5.13 Antiviral activity against SARS COV-2 infected in monkey vero cells assessed as ... 33894564

Literature References

PubMed DOI Target Context # Activities
36229406 10.1021/acs.jmedchem.2c01081 SARS-CoV-2 7
33186044 10.1021/acs.jmedchem.0c01140 ADMET 7
31790578 10.1021/acs.jmedchem.9b01483 Mitochondrial amidoxime-reducing component 1 2
31790578 10.1021/acs.jmedchem.9b01483 Mitochondrial amidoxime reducing component 2 2
36764470 10.1016/j.bmcl.2023.129174 Influenza A virus 2
33186044 10.1021/acs.jmedchem.0c01140 SARS-CoV-2 2
39235978 10.1021/acs.jmedchem.4c01346 Chikungunya virus 1
22991951 10.1021/jm301176r Plasmodium falciparum 1
36764470 10.1016/j.bmcl.2023.129174 MDCK 1
36764470 10.1016/j.bmcl.2023.129174 SARS-CoV-2 1
36764470 10.1016/j.bmcl.2023.129174 Vero 1
33186044 10.1021/acs.jmedchem.0c01140 Middle East respiratory syndrome-related coronavirus 1
33186044 10.1021/acs.jmedchem.0c01140 SARS-CoV 1
33186044 10.1021/acs.jmedchem.0c01140 Vero C1008 1
36229406 10.1021/acs.jmedchem.2c01081 Unchecked 1
36229406 10.1021/acs.jmedchem.2c01081 Middle East respiratory syndrome-related coronavirus 1
36229406 10.1021/acs.jmedchem.2c01081 SARS-CoV 1
36229406 10.1021/acs.jmedchem.2c01081 Vero C1008 1
36229406 10.1021/acs.jmedchem.2c01081 HEK-293T 1
33894564 10.1016/j.ejmech.2021.113467 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine