Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H13N5O3 |
| Molecular Weight | 251.2419 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)C[C@H]3O
InChI
InChIKey=OFEZSBMBBKLLBJ-BAJZRUMYSA-N
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
| Molecular Formula | C10H13N5O3 |
| Molecular Weight | 251.2419 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26443809 | https://www.ncbi.nlm.nih.gov/pubmed/8667637
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26443809 | https://www.ncbi.nlm.nih.gov/pubmed/8667637
Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the absence of the hydroxy group in the 3' position of its ribose part. Cytostatic effect of cordycepin is due to incorporation of phospho-cordycepin into mRNA and inhibition of mRNA synthesis. Cordycepin exhibit rapid antidepressant effect due to potentiation of AMPA receptors
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map03020 |
50.0 µM [Ki] | ||
Target ID: P04053 Gene ID: 1791.0 Gene Symbol: DNTT Target Organism: Homo sapiens (Human) |
21.0 µM [IC50] | ||
Target ID: P42261 Gene ID: 2890.0 Gene Symbol: GRIA1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain. | 2009-02 |
|
| GAL4 GFP enhancer trap lines for analysis of stomatal guard cell development and gene expression. | 2009 |
|
| Cordycepin inhibits vascular smooth muscle cell proliferation. | 2008-11-12 |
|
| Effects of sample preparation methods on the quantification of nucleosides in natural and cultured Cordyceps. | 2008-09-10 |
|
| A molecular circuit composed of CPEB-1 and c-Jun controls growth hormone-mediated synaptic plasticity in the mouse hippocampus. | 2008-08-20 |
|
| Heat stress enhances the accumulation of polyadenylated mitochondrial transcripts in Arabidopsis thaliana. | 2008-08-06 |
|
| Proteomic detection of changes in protein expression induced by cordycepin in human hepatocellular carcinoma BEL-7402 cells. | 2008-06 |
|
| Simple HPLC-UV determination of nucleosides and its application to the authentication of Cordyceps and its allies. | 2008-06 |
|
| Cordycepin (3'-deoxyadenosine) inhibits the growth of B16-BL6 mouse melanoma cells through the stimulation of adenosine A3 receptor followed by glycogen synthase kinase-3beta activation and cyclin D1 suppression. | 2008-06 |
|
| Cordyceps: a traditional Chinese medicine and another fungal therapeutic biofactory? | 2008-05 |
|
| Effects of Cordyceps sinensis, Cordyceps militaris and their isolated compounds on ion transport in Calu-3 human airway epithelial cells. | 2008-04-17 |
|
| PAP inhibitor with in vivo efficacy identified by Candida albicans genetic profiling of natural products. | 2008-04 |
|
| The effect of the polyadenylation inhibitor cordycepin on human Molt-4 and Daudi leukaemia and lymphoma cell lines. | 2008-04 |
|
| RNA-directed agent, cordycepin, induces cell death in multiple myeloma cells. | 2008-03 |
|
| Adenosine kinase mediates high affinity adenosine salvage in Trypanosoma brucei. | 2008-02-29 |
|
| Isolation of a strong Arabidopsis guard cell promoter and its potential as a research tool. | 2008-02-19 |
|
| A Phytochemically characterized extract of Cordyceps militaris and cordycepin protect hippocampal neurons from ischemic injury in gerbils. | 2008-02 |
|
| The role of cordycepin in cancer treatment via induction or inhibition of apoptosis: implication of polyadenylation in a cell type specific manner. | 2008-02 |
|
| Effect of Cordyceps militaris supplementation on sperm production, sperm motility and hormones in Sprague-Dawley rats. | 2008 |
|
| Synthesis and properties of (alpha-P-borano)-nucleoside 5'-triphosphate analogues as potential antiviral agents. | 2008 |
|
| Cordycepin induced eryptosis in mouse erythrocytes through a Ca2+-dependent pathway without caspase-3 activation. | 2007-12 |
|
| Cordycepin/Hydroxyurea synergy allows low dosage efficacy of cordycepin in MOLT-4 leukemia cells. | 2007-11-01 |
|
| Effects of ammonium feeding on the production of bioactive metabolites (cordycepin and exopolysaccharides) in mycelial culture of a Cordyceps sinensis fungus. | 2007-11 |
|
| [Quantitative analysis of adenosine and cordycepin in Cordyceps sinensis and its substitutes with LC-MS-MS]. | 2007-10 |
|
| Inhibitory effects of cordycepin (3'-deoxyadenosine), a component of Cordyceps militaris, on human platelet aggregation induced by thapsigargin. | 2007-07 |
|
| Role of the stage-regulated nucleoside transporter TbNT10 in differentiation and adenosine uptake in Trypanosoma brucei. | 2007-07 |
|
| Optimization of CEC for simultaneous determination of eleven nucleosides and nucleobases in Cordyceps using central composite design. | 2007-06 |
|
| The apoptotic effect of cordycepin on human OEC-M1 oral cancer cell line. | 2007-06 |
|
| Reinforcement of antitumor effect of Cordyceps sinensis by 2'-deoxycoformycin, an adenosine deaminase inhibitor. | 2007-04-18 |
|
| Cordycepin (3'-deoxyadenosine) inhibits human platelet aggregation in a cyclic AMP- and cyclic GMP-dependent manner. | 2007-03-08 |
|
| [Study on HPEC fingerprint of cultured Cordyceps militaris]. | 2007-01 |
|
| Inhibitory effects of ethyl acetate extract of Cordyceps sinensis mycelium on various cancer cells in culture and B16 melanoma in C57BL/6 mice. | 2007-01 |
|
| Improvement of sperm production in subfertile boars by Cordyceps militaris supplement. | 2007 |
|
| Organ-specific, developmental, hormonal and stress regulation of expression of putative pectate lyase genes in Arabidopsis. | 2007 |
|
| Synthesis and properties of cordycepin intercalates of Mg-Al-nitrate layered double hydroxides. | 2006-12-01 |
|
| Cordycepin (3'-deoxyadenosine) inhibits human platelet aggregation induced by U46619, a TXA2 analogue. | 2006-12 |
|
| The effect of Zn on the Zn accumulation and biosynthesis of amino acids in mycelia of Cordyceps sinensis. | 2006-10 |
|
| Cordycepin inhibits lipopolysaccharide-induced inflammation by the suppression of NF-kappaB through Akt and p38 inhibition in RAW 264.7 macrophage cells. | 2006-09-18 |
|
| Mycelium cultivation, chemical composition and antitumour activity of a Tolypocladium sp. fungus isolated from wild Cordyceps sinensis. | 2006-08 |
|
| Cytoplasmic polyadenylation controls cdc25B mRNA translation in rat oocytes resuming meiosis. | 2006-07 |
|
| Quality evaluation of Cordyceps through simultaneous determination of eleven nucleosides and bases by RP-HPLC. | 2006-05 |
|
| Comparison of protective effects between cultured Cordyceps militaris and natural Cordyceps sinensis against oxidative damage. | 2006-04-19 |
|
| Identification and determination of nucleosides in Cordyceps sinensis and its substitutes by high performance liquid chromatography with mass spectrometric detection. | 2006-02-24 |
|
| Antitumor effect of cordycepin (3'-deoxyadenosine) on mouse melanoma and lung carcinoma cells involves adenosine A3 receptor stimulation. | 2006-02-16 |
|
| Pharmacological actions of Cordyceps, a prized folk medicine. | 2005-12 |
|
| Treatment of African trypanosomiasis with cordycepin and adenosine deaminase inhibitors in a mouse model. | 2005-11-01 |
|
| Synthesis of 4'-substituted cordycepins. | 2005 |
|
| Effect of cordycepin on Hantaan virus 76-118 infection of primary human embryonic pulmonary fibroblasts--characterization of apoptotic effects. | 2005 |
|
| A comparative study on the production of exopolysaccharides between two entomopathogenic fungi Cordyceps militaris and Cordyceps sinensis in submerged mycelial cultures. | 2005 |
|
| Measurement of cordycepin and adenosine in stroma of Cordyceps sp. by capillary zone electrophoresis (CZE). | 2002 |
Sample Use Guides
Cordycepin is administred via IV infusions at escalating doses starting from 6mg/m2
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
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Mon Mar 31 17:54:00 GMT 2025
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Mon Mar 31 17:54:00 GMT 2025
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| Record UNII |
GZ8VF4M2J8
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Validated (UNII)
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FDA ORPHAN DRUG |
242507
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NCI_THESAURUS |
C1556
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m3784
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C058120
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GZ8VF4M2J8
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CORDYCEPIN
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1989289
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
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