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Cordycepin

AlkaPlorer ID: AK001196

Synonym: None

IUPAC Name: (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

Structure

SMILES: NC1=C2N=CN([C@@H]3O[C@H](CO)C[C@H]3O)C2=NC=N1

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InChI: InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1

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InChIKey: OFEZSBMBBKLLBJ-BAJZRUMYSA-N

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Properties Information

Molecule Weight: 251.246

TPSA？: 119.31

MolLogP？: -0.9508000000000004

Number of H-Donors: 3

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Adenosine deaminase Stability nan % 10.1021/acs.jmedchem.2c01348
Candida albicans (strain WO-1) (Yeast) ATP-dependent molecular chaperone HSP82 EC50 150000.0 nM None
Chlorocebus sabaeus Vero IC50 0.5 nM 10.1021/jm981132u
Coxsackievirus B4 Coxsackievirus B4 MIC 100.0 ug.mL-1 10.1021/jm00102a010
Hepacivirus hominis Hepatitis C virus EC50 70000.0 nM 10.1016/j.bmc.2014.08.024
Hepatitis C virus Hepatitis C virus NS5B RNA-dependent RNA polymerase EC50 46000.0 nM 10.1021/jm030424e
Hepatitis C virus Hepatitis C virus NS5B RNA-dependent RNA polymerase IC50 22000.0 nM 10.1021/jm030424e
Homo sapiens Adenosine deaminase Drug metabolism nan None 10.1021/jm401530a
Homo sapiens BXPC-3 Imax 22.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens BXPC-3 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens CCRF-CEM FC 2.0 None 10.1021/acs.jmedchem.2c01348
Homo sapiens CCRF-CEM FC 16.0 None 10.1021/acs.jmedchem.2c01348
Homo sapiens CCRF-CEM Imax 12.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens CCRF-CEM LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens HEL 92.1.7 Imax 88.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens HEL 92.1.7 LC50 68900.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens HepG2 IC50 100000.0 nM 10.6019/CHEMBL3430912
Homo sapiens HepG2 Imax 66.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens HepG2 LC50 142470.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens Histone deacetylase 6 Inhibition -9.63 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 4.37 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 Imax 88.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens HL-60 LC50 76840.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens HT-29 Imax 44.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens HT-29 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens Jurkat Imax 20.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens Jurkat LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens K562 Imax 88.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens K562 LC50 59310.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens KG-1 Imax 78.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens KG-1 LC50 70820.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens MCF7 Imax 78.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens MCF7 LC50 34230.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens MIA PaCa-2 Imax 35.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens MIA PaCa-2 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens MOLT-4 IC50 100.0 nM 10.1021/jm401530a
Homo sapiens MOLT-4 IC50 100000.0 nM 10.1021/jm401530a
Homo sapiens MOLT-4 Imax 52.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens MOLT-4 LC50 151920.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens MT4 CD50 45.0 uM 10.1021/jm00118a033
Homo sapiens MT4 Selectivity index 0.5 None 10.1021/jm00118a033
Homo sapiens MV4-11 Imax 1.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens MV4-11 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens NCI-H929 Imax 24.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens NCI-H929 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens RL FC 2.0 None 10.1021/acs.jmedchem.2c01348
Homo sapiens RL Imax 17.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens RL LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens RPMI-8226 Imax 1.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens RPMI-8226 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens SW-620 Imax 10.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens SW-620 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens THP-1 Imax -3.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens THP-1 LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 7307.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 8199.5 nM None
Homo sapiens Z-138 Imax 95.0 % 10.1021/acs.jmedchem.2c01348
Homo sapiens Z-138 LC50 12150.0 nM 10.1021/acs.jmedchem.2c01348
Human alphaherpesvirus 1 Human alphaherpesvirus 1 MIC 40.0 ug.mL-1 10.1021/jm00102a010
Human alphaherpesvirus 2 Human alphaherpesvirus 2 MIC 40.0 ug.mL-1 10.1021/jm00102a010
Human immunodeficiency virus 1 Human immunodeficiency virus 1 ED50 50.0 uM 10.1021/jm00118a033
Human immunodeficiency virus 1 Human immunodeficiency virus 1 MIC 4.0 ug.mL-1 10.1021/jm00102a010
Human respirovirus 3 Human respirovirus 3 MIC 100.0 ug.mL-1 10.1021/jm00102a010
Leishmania donovani Leishmania donovani IC50 50118.72 nM 10.6019/CHEMBL3430912
Mammalian orthoreovirus 1 Mammalian orthoreovirus 1 MIC 100.0 ug.mL-1 10.1021/jm00102a010
Mus musculus L929 IC50 28700.0 nM 10.1021/jm401530a
Mus musculus Mus musculus AUC 4824.0 ng.hr.mL-1 10.1016/j.ejmech.2008.05.013
Mus musculus Mus musculus Cmax 10100.0 nM 10.1016/j.ejmech.2008.05.013
Mus musculus Mus musculus T1/2 2.1 hr 10.1016/j.ejmech.2008.05.013
Mus musculus Mus musculus Tmax 1.5 hr 10.1016/j.ejmech.2008.05.013
Mus musculus NIH3T3 IC50 50118.72 nM 10.6019/CHEMBL3430912
Mus musculus Toll-like receptor 4 Inhibition nan % 10.1021/acs.jnatprod.5b00573
Mus musculus Transcription factor p65 Inhibition nan % 10.1016/j.bmc.2012.10.047
Plasmodium falciparum Plasmodium falciparum IC50 4.5 ug.mL-1 10.1021/np0401415
Poliovirus 1 Poliovirus 1 MIC 100.0 ug.mL-1 10.1021/jm00102a010
Rattus norvegicus Adenosine A1 receptor Ki 7120.0 nM 10.1021/jm00020a014
Rattus norvegicus Adenosine A1 receptor Ki 7120.0 nM 10.1021/jm970176k
Rattus norvegicus Adenosine A1 receptor Ki 15200.0 nM 10.1021/jm00020a014
Rattus norvegicus Adenosine A1 receptor Ki 15200.0 nM 10.1021/jm970176k
Rattus norvegicus Adenosine A1 receptor Ratio 2.1 None 10.1021/jm970176k
Rattus norvegicus Rattus norvegicus GTP shift 2.1 None 10.1021/jm00020a014
Saccharomyces cerevisiae S288c Mitochondrial import inner membrane translocase subunit TIM23 IC50 14000.0 nM None
Semliki Forest virus Semliki Forest virus MIC 100.0 ug.mL-1 10.1021/jm00102a010
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 16.8 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 19.48 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.0 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.03 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 14.13 % 10.21203/rs.3.rs-23951/v1
Sindbis virus Sindbis virus MIC 100.0 ug.mL-1 10.1021/jm00102a010
Trichomonas vaginalis Trichomonas vaginalis GI 94.1 % 10.1016/j.bmcl.2012.03.087
Trypanosoma brucei Trypanosoma brucei IC50 1.2 nM 10.1021/jm401530a
Trypanosoma brucei Trypanosoma brucei IC50 32.0 nM 10.1021/jm401530a
Trypanosoma brucei Trypanosoma brucei IC50 42.0 nM 10.1021/jm401530a
Trypanosoma brucei brucei Trypanosoma brucei brucei Activity nan None 10.1021/jm401530a
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 10.0 nM 10.6019/CHEMBL3430912
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 12.59 nM 10.6019/CHEMBL3430912
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 30.0 nM 10.1021/jm401530a
Trypanosoma cruzi Trypanosoma cruzi EC50 2510.0 nM 10.1021/acs.jmedchem.8b00999
Trypanosoma cruzi Trypanosoma cruzi IC50 1122.02 nM 10.6019/CHEMBL3430912
Trypanosoma cruzi Trypanosoma cruzi IC50 1258.93 nM 10.6019/CHEMBL3430912
Trypanosoma cruzi Trypanosoma cruzi IC50 1995.26 nM 10.6019/CHEMBL3430912
Trypanosoma cruzi Trypanosoma cruzi IC50 5011.87 nM 10.6019/CHEMBL3430912
Trypanosoma cruzi (strain CL Brener) Sterol 14-alpha demethylase IC50 100000.0 nM 10.6019/CHEMBL3430912
Vaccinia virus Vaccinia virus MIC 100.0 ug.mL-1 10.1021/jm00102a010
Vesicular stomatitis virus Vesicular stomatitis virus MIC 40.0 ug.mL-1 10.1021/jm00102a010
Vesicular stomatitis virus Vesicular stomatitis virus MIC 100.0 ug.mL-1 10.1021/jm00102a010
None ADMET Binding energy 8.2 kCal mol-1 10.1021/jm00378a021
None ADMET CC50 13000.0 nM 10.1016/j.bmc.2014.08.024
None ADMET FC 19.0 None 10.1021/acs.jmedchem.2c01348
None ADMET FC 38.0 None 10.1021/acs.jmedchem.2c01348
None ADMET Ratio EC50 25.0 None 10.1021/acs.jmedchem.8b00999
None ADMET Stability 42.1 % 10.1021/acs.jmedchem.2c01348
None ADMET Stability nan % 10.1021/acs.jmedchem.2c01348
None ADMET T1/2 0.4167 hr 10.1021/acs.jmedchem.2c01348
None ADMET T1/2 1.033 hr 10.1021/acs.jmedchem.2c01348
None ADMET T1/2 4.2 hr 10.1021/acs.jmedchem.2c01348
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None No relevant target Drug metabolism 0.012 L/mol/min 10.1021/acs.jmedchem.1c00790
None Unchecked Activity nan None 10.1021/acs.jmedchem.2c01348
None Unchecked EC50 4100.0 nM None
None Unchecked EC50 64000.0 nM 10.1021/acs.jmedchem.8b00999
None Unchecked EC50 150000.0 nM None
None Unchecked Imax 2.0 % 10.1021/acs.jmedchem.2c01348
None Unchecked Ki 180.0 nM 10.1021/jm401530a
None Unchecked LC50 198000.0 nM 10.1021/acs.jmedchem.2c01348
None Unchecked Potency 4466.8 nM None
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 44668.4 nM None
None Unchecked Ratio CC50/EC50 0.19 None 10.1016/j.bmc.2014.08.024

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT021664 Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)C[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)C[C@H]1O enzymemap_43524
AKRT021703 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)C[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)C[C@H]1O enzymemap_45278