Cytidine
AlkaPlorer ID: AK001153
Synonym: None
IUPAC Name: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Structure
SMILES: N=C1C=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(O)=N1
InChI: InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
InChIKey: UHDGCWIWMRVCDJ-XVFCMESISA-N
Reference
PubChem CID: 123837539
CAS: 4395-95-3
LOTUS: LTS0075123
SuperNatural Ⅲ: SN0370328-13
NPASS: NPC62927
Source
Properties Information
Molecule Weight: 243.219
TPSA?: 131.82000000000002
MolLogP?: -2.32033
Number of H-Donors: 5
Number of H-Acceptors: 8
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Cavia porcellus | Ileum | Activity | 0.0 | % | 10.1021/np50060a041 |
| Cavia porcellus | Ileum | Inhibition | 0.0 | % | 10.1021/np50060a041 |
| Cryptosporidium parvum | Cryptosporidium parvum | Inhibition | 73.84 | % | 10.6019/CHEMBL3137356 |
| Entamoeba histolytica | Entamoeba histolytica | IC50 | 30000.0 | nM | 10.6019/CHEMBL3301448 |
| Hepacivirus hominis | Hepatitis C virus | EC50 | 50000.0 | nM | 10.1016/j.bmcl.2022.128605 |
| Homo sapiens | 786-0 | Inhibition | 95.21 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | A498 | Inhibition | 106.14 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | ACHN | Inhibition | 79.47 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | BT-549 | Inhibition | 111.03 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | CAKI-1 | Inhibition | 91.32 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | CCRF-CEM | Inhibition | 29.17 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Chromobox protein homolog 1 | Potency | 56234.1 | nM | None |
| Homo sapiens | COLO 205 | Inhibition | 109.56 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Cytidine deaminase | Kcat | 5.4 | /s | 10.1128/aac.01184-07 |
| Homo sapiens | Cytidine deaminase | Kcat/Km | 0.14 | /uM/s | 10.1128/aac.01184-07 |
| Homo sapiens | Cytidine deaminase | Km | 40000.0 | nM | 10.1128/aac.01184-07 |
| Homo sapiens | Deoxycytidine kinase | Kcat | 0.009 | /s | 10.1128/aac.00400-06 |
| Homo sapiens | Deoxycytidine kinase | Kcat/Km | 0.0014 | /uM/s | 10.1128/aac.00400-06 |
| Homo sapiens | Deoxycytidine kinase | Km | 6600.0 | nM | 10.1128/aac.00400-06 |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 354.8 | nM | None |
| Homo sapiens | DU-145 | Inhibition | 94.37 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Glucose transporter | IC50 | 12000.0 | nM | 10.6019/CHEMBL3433997 |
| Homo sapiens | HCT-116 | Inhibition | 64.35 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | HERG | Inhibition | 0.0 | % | 10.6019/CHEMBL3301458 |
| Homo sapiens | HERG | Inhibition | 8.0 | % | 10.6019/CHEMBL3301458 |
| Homo sapiens | HL-60(TB) | Inhibition | 99.75 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | HOP-62 | Inhibition | 65.03 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | HOP-92 | Inhibition | 73.17 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | HOS-TE85 | IC50 | 2.6 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | IGROV-1 | Inhibition | 82.92 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | KHOS-321H | IC50 | 0.27 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | KM12 | Inhibition | 72.08 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | M14 | Inhibition | 107.42 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Malme-3M | Inhibition | 108.64 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | MCF7 | Inhibition | 63.14 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | MDA-MB-435 | Inhibition | 88.77 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | MDA-MB-468 | Inhibition | 96.83 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | MKN-28 | IC50 | 4.5 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | MOLT-4 | Inhibition | 57.13 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | MRC5 | IC50 | 32000.0 | nM | 10.6019/CHEMBL2028040 |
| Homo sapiens | NCI/ADR-RES | Inhibition | 70.08 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | NCI-H23 | Inhibition | 71.8 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | NCI-H322M | Inhibition | 113.94 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | NCI-H460 | Inhibition | 59.76 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | NCI-H522 | Inhibition | 71.21 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | NUGC-4 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | OST | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | OVCAR-3 | Inhibition | 88.71 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | OVCAR-4 | Inhibition | 72.27 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | OVCAR-5 | Inhibition | 104.12 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | OVCAR-8 | Inhibition | 58.47 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | PC-13 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | PC-3 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | PC-3 | Inhibition | 85.57 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | PC-8 | IC50 | 0.28 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | PC-9 | IC50 | 1.6 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | QG-56 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | RPMI-8226 | Inhibition | 49.81 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | RXF 393 | Inhibition | 50.13 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SF-268 | Inhibition | 86.2 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SF-295 | Inhibition | 58.55 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SF-539 | Inhibition | 73.13 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SK-ES1 | IC50 | 0.09 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | SK-MEL-2 | Inhibition | 110.42 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SK-MEL-28 | Inhibition | 76.39 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SK-MEL-5 | Inhibition | 89.92 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SK-OV-3 | Inhibition | 90.21 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SN12C | Inhibition | 54.88 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SNB-19 | Inhibition | 101.28 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | SNB-75 | Inhibition | 76.88 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Solute carrier organic anion transporter family member 1B1 | Inhibition | 99.44 | % | 10.1124/mol.112.084152 |
| Homo sapiens | Solute carrier organic anion transporter family member 1B3 | Inhibition | 114.03 | % | 10.1124/mol.112.084152 |
| Homo sapiens | SR | Inhibition | 2.991 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | ST-KM-1 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | SW480 | IC50 | 100.0 | ug.mL-1 | 10.1021/jm00113a034 |
| Homo sapiens | SW-620 | Inhibition | 72.7 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | TK-10 | Inhibition | 124.52 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | U-251 | Inhibition | 48.89 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | UACC-257 | Inhibition | 90.08 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | UACC-62 | Inhibition | 95.91 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | UO-31 | Inhibition | 100.43 | % | 10.6019/CHEMBL3301486 |
| Homo sapiens | Uridine-cytidine kinase 1 | Kcat | 0.5 | /s | 10.1128/aac.00400-06 |
| Homo sapiens | Uridine-cytidine kinase 1 | Kcat/Km | 0.0038 | /uM/s | 10.1128/aac.00400-06 |
| Homo sapiens | Uridine-cytidine kinase 1 | Km | 131000.0 | nM | 10.1128/aac.00400-06 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | -6900.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | -3700.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | -1800.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | -700.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | 600.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | 1400.0 | % | 10.6019/CHEMBL3301472 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Inhibition | 2700.0 | % | 10.6019/CHEMBL3301472 |
| Leishmania infantum | Leishmania infantum | IC50 | 32000.0 | nM | 10.6019/CHEMBL2028040 |
| Leishmania mexicana | Glucose transporter | IC50 | 12000.0 | nM | 10.6019/CHEMBL3433997 |
| Mus musculus | Cytidine deaminase | Relative initial rate | 100.0 | None | 10.1021/jm00356a032 |
| Mus musculus | L1210 | Concentration | 0.0001 | M | 10.1021/jm00382a006 |
| Mus musculus | L1210 | Concentration | 0.001 | M | 10.1021/jm00382a006 |
| Mus musculus | Sarcoma-180 | Phosphorylating activity | 812.0 | pM min-1 assay-1 | 10.1021/jm9801814 |
| Mycobacterium tuberculosis | Mycobacterium tuberculosis | Inhibition | -3.06 | % | 10.6019/CHEMBL2094260 |
| Mycobacterium tuberculosis | Mycobacterium tuberculosis | Inhibition | 14.6 | % | 10.6019/CHEMBL2094260 |
| Onchocerca lienalis | Onchocerca lienalis | Motility | 100.0 | % | 10.6019/CHEMBL3137381 |
| Plasmodium berghei | Plasmodium berghei | Inhibition | -17.3 | % | 10.6019/CHEMBL3301451 |
| Plasmodium falciparum | Calcium-dependent protein kinase 1 | IC50 | 1000.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum | Cdk-related protein kinase 6 | IC50 | 1000.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum | Hexose transporter 1 | IC50 | 12000.0 | nM | 10.6019/CHEMBL3433997 |
| Plasmodium falciparum | Mitogen-activated protein kinase | IC50 | 1000.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum | Plasmodium falciparum | EC50 | 385.0 | nM | 10.6019/CHEMBL2028040 |
| Plasmodium falciparum | Plasmodium falciparum | Growth Inhibition | 13.52 | % | 10.6019/CHEMBL3301555 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | -25.67 | % | 10.6019/CHEMBL3301451 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | -18.78 | % | 10.6019/CHEMBL3301451 |
| Plasmodium falciparum | Plasmodium falciparum | Ratio | 0.6667 | None | 10.6019/CHEMBL2448809 |
| Plasmodium falciparum | Putative uncharacterized protein pk7 | IC50 | 1000.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum (isolate 3D7) | Calcium-dependent protein kinase 4 | IC50 | 1000.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum (isolate 3D7) | Lysine--tRNA ligase | IC50 | 2500.0 | nM | 10.6019/CHEMBL3301562 |
| Plasmodium falciparum (isolate 3D7) | Proline--tRNA ligase | IC50 | 2500.0 | nM | 10.6019/CHEMBL3301562 |
| Rattus norvegicus | Thymidine kinase | Inhibition | 1.0 | % | 10.1021/jm00348a007 |
| Rattus norvegicus | Thymidine kinase 2 | Inhibition | 13.0 | % | 10.1021/jm00348a007 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | Relative Growth | -0.4063 | None | 10.6019/CHEMBL3301546 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | Relative Growth | -0.0768 | None | 10.6019/CHEMBL3301546 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | Relative Growth | 0.1163 | None | 10.6019/CHEMBL3301546 |
| Schistosoma mansoni | Schistosoma mansoni | Toxicity | 0.0 | None | 10.6019/CHEMBL2363022 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 7.65 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | -0.08 | % | 10.6019/CHEMBL4495565 |
| Streptomyces avidinii | Streptavidin | Activity | nan | None | 10.1016/j.bmcl.2012.09.088 |
| Toxoplasma gondii | Toxoplasma gondii | IC50 | 30000.0 | nM | 10.6019/CHEMBL3301448 |
| Trypanosoma brucei brucei | Trypanosoma brucei brucei | IC50 | 32000.0 | nM | 10.6019/CHEMBL2028040 |
| Trypanosoma brucei rhodesiense | Trypanosoma brucei rhodesiense | IC50 | 32000.0 | nM | 10.6019/CHEMBL2028040 |
| Trypanosoma cruzi | Trypanosoma cruzi | IC50 | 32000.0 | nM | 10.6019/CHEMBL2028040 |
| None | ADMET | Km | 50000.0 | nM | 10.1021/jm00138a003 |
| None | NON-PROTEIN TARGET | % Cell Death | -30.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | % Cell Death | -9.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | % Cell Death | 0.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | % Cell Death | 24.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | % Cell Death | 26.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | % Cell Death | 28.0 | None | 10.6019/CHEMBL3301472 |
| None | NON-PROTEIN TARGET | IC50 | 30000.0 | nM | 10.1021/np0495985 |
| None | No relevant target | LogP | -2.29 | None | 10.1021/jm00090a008 |
| None | Radical scavenging activity | IC50 | 30000.0 | nM | 10.1021/np0495985 |
| None | Unchecked | IC50 | 4270.0 | nM | 10.6019/CHEMBL3301464 |
| None | Unchecked | IC50 | 7310.0 | nM | 10.6019/CHEMBL3301464 |
| None | Unchecked | IC50 | 14090.0 | nM | 10.6019/CHEMBL3301464 |
| None | Unchecked | IC50 | 19130.0 | nM | 10.6019/CHEMBL3301464 |
| None | Unchecked | Inhibition | 46.59 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 74.3 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 75.53 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 82.83 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 98.98 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 99.17 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 105.57 | % | 10.6019/CHEMBL3301486 |
| None | Unchecked | Inhibition | 105.62 | % | 10.6019/CHEMBL3301486 |
