30925
Cordycepin
≥98.0% (HPLC)
Synonym(s):
3′-Deoxyadenosine
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
Molecular Weight:
251.24
EC Number:
200-791-4
UNSPSC Code:
12352203
PubChem Substance ID:
Beilstein/REAXYS Number:
35194
MDL number:
InChI key
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
SMILES string
Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)C[C@H]3O
assay
≥98.0% (HPLC)
mp
225-229 °C
antibiotic activity spectrum
fungi
mode of action
DNA synthesis | interferes, enzyme | inhibits
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General description
Chemical structure: nucleoside
Biochem/physiol Actions
Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.
Other Notes
Starting material for the synthesis of cordycepin triphosphate, an inhibitor of replicative synthesis
Regulatory Information
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Hardeep S Tuli et al.
Life sciences, 93(23), 863-869 (2013-10-15)
Cytotoxic nucleoside analogues were the first chemotherapeutic agents for cancer treatment. Cordycepin, an active ingredient of the insect fungus Cordyceps militaris, is a category of compounds that exhibit significant therapeutic potential. Cordycepin has many intracellular targets, including nucleic acid (DNA/RNA)
Wei Su et al.
RNA (New York, N.Y.), 19(1), 1-16 (2012-11-29)
Metazoan replication-dependent histone mRNAs are only present in S-phase, due partly to changes in their stability. These mRNAs end in a unique stem-loop (SL) that is required for both translation and cell-cycle regulation. Previous studies showed that histone mRNA degradation
Thiyagarajan Ramesh et al.
Experimental gerontology, 47(12), 979-987 (2012-09-25)
Free radical-induced oxidative damage is considered to be the most important consequence of the aging process. The activities and capacities of antioxidant systems of cells decline with increased age, leading to the gradual loss of pro-oxidant/antioxidant balance and resulting in
Alexander Kondrashov et al.
RNA (New York, N.Y.), 18(12), 2236-2250 (2012-11-03)
Cordycepin (3' deoxyadenosine) has long been used in the study of in vitro assembled polyadenylation complexes, because it terminates the poly(A) tail and arrests the cleavage complex. It is derived from caterpillar fungi, which are highly prized in Chinese traditional
R I Gumport et al.
Biochemistry, 15(13), 2804-2809 (1976-06-29)
A structural analogue of ATP, 3'-deoxyadenosine triphosphate (3'-dATP), has been synthesized from cordycepin (3'-deoxyadenosine), characterized, and determined to be an inhibitor of ATP-dependent DNA synthesis in Escherichia coli cells which have been reduced permeable to nucleoside triphosphates by treatment with
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