CORDYCEPIN

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Search structure


Synonyms	3'-Deoxyadenosine 9-cordyceposidoadenine Cordycepin Cordycepine NSC-401022 NSC-63984
Status
Molecule Category	UNKNOWN
UNII	GZ8VF4M2J8
EPA CompTox	DTXSID1041007


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OFEZSBMBBKLLBJ-BAJZRUMYSA-N
Smiles	Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)C[C@H]1O
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C10H13N5O3
Molecular Weight	251.25
AlogP	-0.95
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	2.0
Polar Surface Area	119.31
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	18.0

Assay Description	Organism	Bioactivity	Reference
Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition assay	Chlorocebus sabaeus	0.5 nM
Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 after 24 hrs by [3H]hypoxanthine uptake	Plasmodium falciparum K1	4.5 ug.mL-1
Trypanocidal activity against bloodstream stage of Trypanosoma brucei after 72 hrs by WST-1 assay in presence of deoxycoformycin	Trypanosoma brucei	1.2 nM
Trypanocidal activity against bloodstream stage of Trypanosoma brucei after 72 hrs by WST-1 assay	Trypanosoma brucei	42.0 nM
Cytotoxicity against human MOLT4 cells assessed as cell viability after 72 hrs by WST-1 assay in presence of deoxycoformycin	Homo sapiens	100.0 nM
Displacement of [2,8-3H]-adenosine from Trypanosoma brucei AT1/P2 expressed in bloodstream stage of Trypanosoma brucei brucei B48	Trypanosoma brucei	180.0 nM
Trypanocidal activity against bloodstream stage of Trypanosoma brucei brucei AnTat1.1E after 72 hrs by WST-1 assay	Trypanosoma brucei brucei	30.0 nM
Trypanocidal activity against Trypanosoma brucei	Trypanosoma brucei	32.0 nM
GSK_TCAKS: pIC50 Trypanosoma brucei viability assay using fluorescence intensity. Assay plates (1536-well) were prepared by dispensing 25nL of compound solution per well using an Echo acoustic dispenser (Labcyte). For single shot assays the final compound concentration was 4.2uM. For potency determinations, eleven-point one in three dilution curves were generated and the top concentration was 42uM. Plates were incubated for 2h at room temperature and resorufin fluorescence was determined using a PerkinElmer ViewLux plate reader (excitation at 528 nm and emission at 590 nm).	Trypanosoma brucei	12.59 nM
GSK_TCAKS: pIC50 Trypanosoma brucei viability assay using luminiscence. Assay plates (1536-well) were prepared. T. brucei cultures were harvested and counted in a CASY cell counter. A parasite suspension was prepared at a final concentration of 5 * 10^4 cells/mL in complete HMI9 medium and 6uL was dispensed to all wells containing compounds using a Multidrop Combi dispenser. 6uL of HMI9 media with 0.4% DMSO were dispensed to control columns. Plates were incubated for 24 h at 37C, 5% CO2 then tempered for 10 min at room temperature. ATP content was quantified by adding 4 uL of CellTiter-Glo Reagent (Promega) according to the manufacturer's instructions. Luminescence was measured using a ViewLux.	Trypanosoma brucei	10.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	14.13 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	19.48 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	16.8 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.0 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.03 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.03 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	29014
ChEMBL	CHEMBL305686
DrugBank	DB12156
FDA SRS	GZ8VF4M2J8
Guide to Pharmacology	4630
KEGG	C08431
PDB	3AD
PubChem	6303
SureChEMBL	SCHEMBL98323
ZINC	ZINC000001319796

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).