Cordycepin
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MedKoo CAT#: 200793

CAS#: 73-03-0

Description: Cordycepin, also known as 3'-Deoxyadenosine, is a purine nucleoside antimetabolite and antibiotic isolated from the fungus Cordyceps militaris with potential antineoplastic activity. Cordycepin is an adenosine analogue, which is readily phosphorylated to its mono-, di-, and triphosphate intracellularly. Triphosphate cordycepin can be incorporated into RNA, and inhibits transcription elongation and RNA synthesis due to the absence of a hydroxyl moiety at the 3' position. Because it can be converted to an inactive metabolite by adenosine deaminase, this agent must be administered with an adenosine deaminase inhibitor in order to be effective. Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro.


Chemical Structure

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Cordycepin
CAS# 73-03-0

Theoretical Analysis

MedKoo Cat#: 200793
Name: Cordycepin
CAS#: 73-03-0
Chemical Formula: C10H13N5O3
Exact Mass: 251.10184
Molecular Weight: 251.24
Elemental Analysis: C, 47.81; H, 5.22; N, 27.87; O, 19.10

Size Price Shipping out time Quantity
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-02-27. Prices are subject to change without notice.

Cordycepin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Synonym: 3Deoxyadenosine; 9(3DeoxyDribofuranosyl)adenine

IUPAC/Chemical Name: (2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol

InChi Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N

InChi Code: 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 Code: O[C@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](CO)C1

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 251.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Wang XA, Xiang SS, Li HF, Wu XS, Li ML, Shu YJ, Zhang F, Cao Y, Ye YY, Bao RF, Weng H, Wu WG, Mu JS, Hu YP, Jiang L, Tan ZJ, Lu W, Wang P, Liu YB. Cordycepin induces s phase arrest and apoptosis in human gallbladder cancer cells. Molecules. 2014 Jul 31;19(8):11350-65. doi: 10.3390/molecules190811350. PubMed PMID: 25090123.

2: Kang C, Wen TC, Kang JC, Meng ZB, Li GR, Hyde KD. Optimization of Large-Scale Culture Conditions for the Production of Cordycepin with Cordyceps militaris by Liquid Static Culture. ScientificWorldJournal. 2014;2014:510627. doi: 10.1155/2014/510627. Epub 2014 Jun 23. PubMed PMID: 25054182; PubMed Central PMCID: PMC4094858.

3: Wu WD, Hu ZM, Shang MJ, Zhao DJ, Zhang CW, Hong DF, Huang DS. Cordycepin Down-Regulates Multiple Drug Resistant (MDR)/HIF-1α through Regulating AMPK/mTORC1 Signaling in GBC-SD Gallbladder Cancer Cells. Int J Mol Sci. 2014 Jul 18;15(7):12778-90. doi: 10.3390/ijms150712778. PubMed PMID: 25046749.

4: Lee DH, Kim HH, Cho HJ, Yu YB, Kang HC, Kim JL, Lee JJ, Park HJ. Cordycepin-Enriched WIB801C from Cordyceps militaris Inhibits Collagen-Induced [Ca(2+)]i Mobilization via cAMP-Dependent Phosphorylation of Inositol 1, 4, 5-Trisphosphate Receptor in Human Platelets. Biomol Ther (Seoul). 2014 May;22(3):223-31. doi: 10.4062/biomolther.2014.025. PubMed PMID: 25009703; PubMed Central PMCID: PMC4060073.

5: Zhang JL, Xu Y, Shen J. Cordycepin Inhibits Lipopolysaccharide (LPS)-Induced Tumor Necrosis Factor (TNF)-α Production via Activating AMP-Activated Protein Kinase (AMPK) Signaling. Int J Mol Sci. 2014 Jul 8;15(7):12119-34. doi: 10.3390/ijms150712119. PubMed PMID: 25007068.

6: Lee DH, Kwon HW, Kim HH, Lim DH, Nam GS, Shin JH, Kim YY, Kim JL, Lee JJ, Kwon HK, Park HJ. Cordycepin-enriched WIB801C from Cordyceps militaris inhibits ADP-induced [Ca(2+)] (i) mobilization and fibrinogen binding via phosphorylation of IP (3)R and VASP. Arch Pharm Res. 2014 Jul 9. [Epub ahead of print] PubMed PMID: 25001901.

7: Lee HH, Kim SO, Kim GY, Moon SK, Kim WJ, Jeong YK, Yoo YH, Choi YH. Involvement of autophagy in cordycepin-induced apoptosis in human prostate carcinoma LNCaP cells. Environ Toxicol Pharmacol. 2014 Jun 14;38(1):239-250. doi: 10.1016/j.etap.2014.06.003. [Epub ahead of print] PubMed PMID: 24973666.

8: Lu H, Li X, Zhang J, Shi H, Zhu X, He X. Effects of cordycepin on HepG2 and EA.hy926 cells: Potential antiproliferative, antimetastatic and anti-angiogenic effects on hepatocellular carcinoma. Oncol Lett. 2014 May;7(5):1556-1562. Epub 2014 Mar 11. PubMed PMID: 24765175; PubMed Central PMCID: PMC3997733.

9: Chen Y, Yang SH, Hueng DY, Syu JP, Liao CC, Wu YC. Cordycepin induces apoptosis of C6 glioma cells through the adenosine 2A receptor-p53-caspase-7-PARP pathway. Chem Biol Interact. 2014 Jun 5;216:17-25. doi: 10.1016/j.cbi.2014.03.010. Epub 2014 Apr 2. PubMed PMID: 24704558.

10: Zhang DN, Guo XY, Yang QH, Chen ZG, Tao LJ. An efficient enzymatic modification of cordycepin in ionic liquids under ultrasonic irradiation. Ultrason Sonochem. 2014 Sep;21(5):1682-7. doi: 10.1016/j.ultsonch.2014.02.023. Epub 2014 Mar 1. PubMed PMID: 24631444.



Additional Information

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the absence of oxygen in the 3' position of its ribose part. It was initially extracted from fungi of genus Cordyceps, but is now produced synthetically. Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two. Therefore, it can participate in certain biochemical reactions (for example, be incorporated into an RNA molecule, thus causing the premature termination of its synthesis). It also has interesting properties as a anti-tumor, anti-fungal, anti-viral, since it has the ability to inhibit protein kinases. As an anti-tumor, searchers constated that it has the capacity to reduce the growth of ascites tumor cell in the Ehrilch mouses, of cervival carcinoma cell and Lewis lung cancer.