MedKoo Cat#: 145764 | Name: Eleutherobin

Description:

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

Eleutherobin is a naturally occurring compound found in Eleutherococcus senticosus (commonly known as Siberian ginseng). It is a sesquiterpene compound that has shown biological activity, particularly in its ability to inhibit protein kinase C (PKC), an enzyme involved in various cellular processes such as cell growth, differentiation, and immune responses. Due to its potential anti-inflammatory and anticancer properties, eleutherobin has been studied for its therapeutic effects.

Chemical Structure

Eleutherobin
Eleutherobin
CAS#174545-76-7

Theoretical Analysis

MedKoo Cat#: 145764

Name: Eleutherobin

CAS#: 174545-76-7

Chemical Formula: C35H48N2O10

Exact Mass: 656.3300

Molecular Weight: 656.77

Elemental Analysis: C, 64.01; H, 7.37; N, 4.27; O, 24.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Eleutherobin;
IUPAC/Chemical Name
(1R,4aR,6S,7S,10R,12aS,Z)-11-((((2R,3S,4R,5R)-3-acetoxy-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)-1-isopropyl-10-methoxy-4,7-dimethyl-1,2,4a,5,6,7,10,12a-octahydro-7,10-epoxybenzo[10]annulen-6-yl (E)-3-(1-methyl-1H-imidazol-4-yl)acrylate
InChi Key
XOPYFXBZMVTEJF-PDACKIITSA-N
InChi Code
1S/C35H48N2O10/c1-20(2)25-10-8-21(3)26-15-29(46-30(40)11-9-24-16-37(6)19-36-24)34(5)12-13-35(42-7,47-34)23(14-27(25)26)17-43-33-32(45-22(4)38)31(41)28(39)18-44-33/h8-9,11-14,16,19-20,25-29,31-33,39,41H,10,15,17-18H2,1-7H3/b11-9+,23-14-/t25-,26+,27-,28-,29+,31-,32+,33-,34+,35-/m1/s1
SMILES Code
[H][C@@]12C[C@H](OC(=O)\C=C\C3=CN(C)C=N3)[C@@]4(C)O[C@](OC)(C=C4)C(CO[C@@H]5OC[C@@H](O)[C@@H](O)[C@@H]5OC(C)=O)=C[C@]1([H])[C@H](CC=C2C)C(C)C
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 656.77 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: Long BH, Carboni JM, Wasserman AJ, Cornell LA, Casazza AM, Jensen PR, Lindel T, Fenical W, Fairchild CR. Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (Taxol). Cancer Res. 1998 Mar 15;58(6):1111-5. PMID: 9515790. 2: Sosonyuk SE, Peshich A, Tutushkina AV, Khlevin DA, Lozinskaya NA, Gracheva YA, Glazunova VA, Osolodkin DI, Semenova MN, Semenov VV, Palyulin VA, Proskurnina MV, Shtil AA, Zefirov NS. Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents. Org Biomol Chem. 2019 Mar 6;17(10):2792-2797. doi: 10.1039/c8ob02915f. PMID: 30793716. 3: Burkhardt I, de Rond T, Chen PY, Moore BS. Ancient plant-like terpene biosynthesis in corals. Nat Chem Biol. 2022 Jun;18(6):664-669. doi: 10.1038/s41589-022-01026-2. Epub 2022 May 23. PMID: 35606558; PMCID: PMC9179088. 4: Berrué F, McCulloch MW, Kerr RG. Marine diterpene glycosides. Bioorg Med Chem. 2011 Nov 15;19(22):6702-19. doi: 10.1016/j.bmc.2011.06.083. Epub 2011 Jul 2. PMID: 21783368. 5: Cao YN, Zheng LL, Wang D, Liang XX, Gao F, Zhou XL. Recent advances in microtubule-stabilizing agents. Eur J Med Chem. 2018 Jan 1;143:806-828. doi: 10.1016/j.ejmech.2017.11.062. Epub 2017 Nov 24. PMID: 29223097. 6: Chen XT, Zhou B, Bhattacharya SK, Gutteridge CE, Pettus TRR, Danishefsky SJ. The Total Synthesis of Eleutherobin: A Surprise Ending. Angew Chem Int Ed Engl. 1998 Apr 3;37(6):789-792. doi: 10.1002/(SICI)1521-3773(19980403)37:6<789::AID- ANIE789>3.0.CO;2-3. PMID: 29711384. 7: McDaid HM, Bhattacharya SK, Chen XT, He L, Shen HJ, Gutteridge CE, Horwitz SB, Danishefsky SJ. Structure-activity profiles of eleutherobin analogs and their cross-resistance in Taxol-resistant cell lines. Cancer Chemother Pharmacol. 1999;44(2):131-7. doi: 10.1007/s002800050957. PMID: 10412947. 8: Li Z, Rudolf JD. Biosynthesis, enzymology, and future of eunicellane diterpenoids. J Ind Microbiol Biotechnol. 2023 Feb 17;50(1):kuad027. doi: 10.1093/jimb/kuad027. PMID: 37673680; PMCID: PMC10548852. 9: Britton R, de Silva ED, Bigg CM, McHardy LM, Roberge M, Andersen RJ. Synthetic transformations of eleutherobin reveal new features of its microtubule-stabilizing pharmacophore. J Am Chem Soc. 2001 Sep 5;123(35):8632-3. doi: 10.1021/ja016459q. PMID: 11525686. 10: Scesa PD, Lin Z, Schmidt EW. Ancient defensive terpene biosynthetic gene clusters in the soft corals. Nat Chem Biol. 2022 Jun;18(6):659-663. doi: 10.1038/s41589-022-01027-1. Epub 2022 May 23. Erratum in: Nat Chem Biol. 2023 Jun;19(6):790. doi: 10.1038/s41589-023-01352-z. PMID: 35606556; PMCID: PMC10262820. 11: Hamel E, Sackett DL, Vourloumis D, Nicolaou KC. The coral-derived natural products eleutherobin and sarcodictyins A and B: effects on the assembly of purified tubulin with and without microtubule-associated proteins and binding at the polymer taxoid site. Biochemistry. 1999 Apr 27;38(17):5490-8. doi: 10.1021/bi983023n. PMID: 10220336. 12: Lindel T. From D-Arabinose to the Marine Natural Product Eleutherobin. Angew Chem Int Ed Engl. 1998 Apr 3;37(6):774-776. doi: 10.1002/(SICI)1521-3773(19980403)37:6<774::AID-ANIE774>3.0.CO;2-R. PMID: 29711381. 13: Chandrasekhar S, Jagadeshwar V, Narsihmulu Ch, Sarangapani M, Krishna DR, Vidyasagar J, Vijay D, Sastry GN. Design, synthesis and cytotoxic studies on the simplified oxy analog of eleutherobin. Bioorg Med Chem Lett. 2004 Jul 16;14(14):3687-9. doi: 10.1016/j.bmcl.2004.05.017. PMID: 15203144. 14: Kingston DG. Tubulin-interactive natural products as anticancer agents. J Nat Prod. 2009 Mar 27;72(3):507-15. doi: 10.1021/np800568j. Erratum in: J Nat Prod. 2011 May 27;74(5):1352. PMID: 19125622; PMCID: PMC2765517. 15: Castoldi D, Caggiano L, Panigada L, Sharon O, Costa AM, Gennari C. A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene. Angew Chem Int Ed Engl. 2005 Jan 14;44(4):588-91. doi: 10.1002/anie.200461767. PMID: 15597390. 16: Busch T, Kirschning A. Recent advances in the total synthesis of pharmaceutically relevant diterpenes. Nat Prod Rep. 2008 Apr;25(2):318-41. doi: 10.1039/b705652b. Epub 2008 Feb 11. PMID: 18389140. 17: Meurer-Grob P, Kasparian J, Wade RH. Microtubule structure at improved resolution. Biochemistry. 2001 Jul 10;40(27):8000-8. doi: 10.1021/bi010343p. PMID: 11434769. 18: Nicolaou KC, Pfefferkorn J, Xu J, Winssinger N, Ohshima T, Kim S, Hosokawa S, Vourloumis D, van Delft F, Li T. Total synthesis and chemical biology of the sarcodictyins. Chem Pharm Bull (Tokyo). 1999 Sep;47(9):1199-213. doi: 10.1248/cpb.47.1199. PMID: 10517002. 19: Alarif WM, Abdel-Lateff A, Alorfi HS, Alburae NA. Alcyonacea: A Potential Source for Production of Nitrogen-Containing Metabolites. Molecules. 2019 Jan 14;24(2):286. doi: 10.3390/molecules24020286. PMID: 30646584; PMCID: PMC6359195. 20: Taglialatela-Scafati O, Deo-Jangra U, Campbell M, Roberge M, Andersen RJ. Diterpenoids from cultured Erythropodium caribaeorum. Org Lett. 2002 Nov 14;4(23):4085-8. doi: 10.1021/ol026831m. PMID: 12423092.