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MedKoo Cat#: 598566 | Name: Eritadenine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.

Chemical Structure

Eritadenine
Eritadenine
CAS#23918-98-1

Theoretical Analysis

MedKoo Cat#: 598566

Name: Eritadenine

CAS#: 23918-98-1

Chemical Formula: C9H11N5O4

Exact Mass: 253.0811

Molecular Weight: 253.21

Elemental Analysis: C, 42.69; H, 4.38; N, 27.66; O, 25.27

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Eritadenine; Lentinacin; Lentysine; D-Eritadenine;
IUPAC/Chemical Name
(2R,3R)-4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid
InChi Key
LIEMBEWXEZJEEZ-INEUFUBQSA-N
InChi Code
InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1
SMILES Code
O=C(O)[C@H](O)[C@H](O)CN1C=NC2=C(N)N=CN=C12
Appearance
Solid powder
Purity
>95% (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
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 253.21 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.

Recalculate based on batch purity %
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
1: Afrin S, Rakib MA, Kim BH, Kim JO, Ha YL. Eritadenine from Edible Mushrooms Inhibits Activity of Angiotensin Converting Enzyme in Vitro. J Agric Food Chem. 2016 Mar 23;64(11):2263-8. doi: 10.1021/acs.jafc.5b05869. Epub 2016 Mar 14. PubMed PMID: 26938194. 2: Shimada Y, Morita T, Sugiyama K. Eritadenine-induced alterations of plasma lipoprotein lipid concentrations and phosphatidylcholine molecular species profile in rats fed cholesterol-free and cholesterol-enriched diets. Biosci Biotechnol Biochem. 2003 May;67(5):996-1006. PubMed PMID: 12834276. 3: Shimada Y, Yamakawa A, Morita T, Sugiyama K. Effects of dietary eritadenine on the liver microsomal Delta6-desaturase activity and its mRNA in rats. Biosci Biotechnol Biochem. 2003 Jun;67(6):1258-66. PubMed PMID: 12843651. 4: Sugiyama K, Akachi T, Yamakawa A. Hypocholesterolemic action of eritadenine is mediated by a modification of hepatic phospholipid metabolism in rats. J Nutr. 1995 Aug;125(8):2134-44. PubMed PMID: 7643248. 5: Ctrnáctá V, Fritzler JM, Surinová M, Hrdý I, Zhu G, Stejskal F. Efficacy of S-adenosylhomocysteine hydrolase inhibitors, D-eritadenine and (S)-DHPA, against the growth of Cryptosporidium parvum in vitro. Exp Parasitol. 2010 Oct;126(2):113-6. doi: 10.1016/j.exppara.2010.04.007. Epub 2010 Apr 20. PubMed PMID: 20412798; PubMed Central PMCID: PMC2914804. 6: Shimada Y, Morita T, Sugiyama K. Dietary eritadenine and ethanolamine depress fatty acid desaturase activities by increasing liver microsomal phosphatidylethanolamine in rats. J Nutr. 2003 Mar;133(3):758-65. PubMed PMID: 12612149. 7: Fukada S, Setoue M, Morita T, Sugiyama K. Dietary eritadenine suppresses guanidinoacetic Acid-induced hyperhomocysteinemia in rats. J Nutr. 2006 Nov;136(11):2797-802. PubMed PMID: 17056803. 8: Yang H, Hwang I, Kim S, Hong EJ, Jeung EB. Lentinus edodes promotes fat removal in hypercholesterolemic mice. Exp Ther Med. 2013 Dec;6(6):1409-1413. Epub 2013 Oct 8. PubMed PMID: 24255670; PubMed Central PMCID: PMC3829752. 9: Enman J, Rova U, Berglund KA. Quantification of the bioactive compound eritadenine in selected strains of shiitake mushroom (Lentinus edodes). J Agric Food Chem. 2007 Feb 21;55(4):1177-80. Epub 2007 Jan 27. PubMed PMID: 17256958. 10: Sugiyama K, Yamakawa A, Kawagishi H, Saeki S. Dietary eritadenine modifies plasma phosphatidylcholine molecular species profile in rats fed different types of fat. J Nutr. 1997 Apr;127(4):593-9. PubMed PMID: 9109610. 11: Sekiya A, Fukada S, Morita T, Kawagishi H, Sugiyama K. Suppression of methionine-induced hyperhomocysteinemia by dietary eritadenine in rats. Biosci Biotechnol Biochem. 2006 Aug;70(8):1987-91. Epub 2006 Aug 1. PubMed PMID: 16880595. 12: Shimada Y, Morita T, Sugiyama K. Effects of dietary eritadenine on delta6-desaturase activity and fatty acid profiles of several lipids in rats fed different fats. Biosci Biotechnol Biochem. 2002 Jul;66(7):1605-9. PubMed PMID: 12224653. 13: Sugiyama K, Yamakawa A. Dietary eritadenine-induced alteration of molecular species composition of phospholipids in rats. Lipids. 1996 Apr;31(4):399-404. PubMed PMID: 8743052. 14: Enman J, Hodge D, Berglund KA, Rova U. Production of the bioactive compound eritadenine by submerged cultivation of shiitake (Lentinus edodes) mycelia. J Agric Food Chem. 2008 Apr 23;56(8):2609-12. doi: 10.1021/jf800091a. Epub 2008 Mar 26. PubMed PMID: 18363329. 15: Sugiyama K, Yamakawa A, Saeki S. Correlation of suppressed linoleic acid metabolism with the hypocholesterolemic action of eritadenine in rats. Lipids. 1997 Aug;32(8):859-66. PubMed PMID: 9270978. 16: Yamada T, Komoto J, Lou K, Ueki A, Hua DH, Sugiyama K, Takata Y, Ogawa H, Takusagawa F. Structure and function of eritadenine and its 3-deaza analogues: potent inhibitors of S-adenosylhomocysteine hydrolase and hypocholesterolemic agents. Biochem Pharmacol. 2007 Apr 1;73(7):981-9. Epub 2006 Dec 14. PubMed PMID: 17214973. 17: Huang Y, Komoto J, Takata Y, Powell DR, Gomi T, Ogawa H, Fujioka M, Takusagawa F. Inhibition of S-adenosylhomocysteine hydrolase by acyclic sugar adenosine analogue D-eritadenine. Crystal structure of S-adenosylhomocysteine hydrolase complexed with D-eritadenine. J Biol Chem. 2002 Mar 1;277(9):7477-82. Epub 2001 Dec 10. PubMed PMID: 11741948. 18: Schanche JS, Schanche T, Ueland PM, Holý A, Votruba I. The effect of aliphatic adenine analogues on S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase in intact rat hepatocytes. Mol Pharmacol. 1984 Nov;26(3):553-8. PubMed PMID: 6493210. 19: Bisen PS, Baghel RK, Sanodiya BS, Thakur GS, Prasad GB. Lentinus edodes: a macrofungus with pharmacological activities. Curr Med Chem. 2010;17(22):2419-30. Review. PubMed PMID: 20491636. 20: Takashima K, Izumi K, Iwai H, Takeyama S. The hypocholesterolemic action of eritadenine in the rat. Atherosclerosis. 1973 May-Jun;17(3):491-502. PubMed PMID: 4736648.