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MedKoo Cat#: 573376 | Name: Elaiophylin
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Description:

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

Elaiophylin is a macrolide antibiotic first isolated from Streptomyces melanosporus. Elaiophylin demonstrates antifungal activity as well as cytotoxicity against mammalian tumor cells, protozoa, and nematodes. This compound has displayed immunosuppressive activity through inhibition of B-cell stimulation and inhibiting proliferation of lymphocytes stimulated by mitogens. Elaiophylin is an inhibitor of 5 α-Reductase and NOS.

Chemical Structure

Elaiophylin
Elaiophylin
CAS#37318-06-2

Theoretical Analysis

MedKoo Cat#: 573376

Name: Elaiophylin

CAS#: 37318-06-2

Chemical Formula: C54H88O18

Exact Mass: 1024.5971

Molecular Weight: 1025.28

Elemental Analysis: C, 63.26; H, 8.65; O, 28.09

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 weeks
5mg USD 950.00 2 weeks
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Synonym
Elaiophylin; Azalomycin B; Gopalamicin; Salbomycin; Antibiotic 5001B
IUPAC/Chemical Name
(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis((2S,3R,4S)-4-((2R,4R,5R,6R)-4-(((2R,4S,5S,6S)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-ethyl-2-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-3-hydroxypentan-2-yl)-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
InChi Key
OSERMIPXNLXAPD-MJMYBOKFSA-N
InChi Code
InChI=1S/C54H88O18/c1-13-37-33(9)71-53(63,25-41(37)67-45-23-39(55)49(61)35(11)65-45)31(7)47(59)29(5)51-27(3)19-15-17-22-44(58)70-52(28(4)20-16-18-21-43(57)69-51)30(6)48(60)32(8)54(64)26-42(38(14-2)34(10)72-54)68-46-24-40(56)50(62)36(12)66-46/h15-22,27-42,45-52,55-56,59-64H,13-14,23-26H2,1-12H3/b19-15+,20-16+,21-18+,22-17+/t27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42+,45-,46-,47+,48+,49+,50+,51-,52-,53+,54+/m0/s1
SMILES Code
O[C@@H]1[C@H](O)[C@H](C)O[C@@]([H])(O[C@H]2[C@H](CC)[C@@H](C)O[C@@](O)([C@@H](C)[C@H](O)[C@H](C)[C@]([H])([C@@H](C)/C=C/C=C/3)OC(/C=C/C=C/[C@H](C)[C@@]([H])([C@@H](C)[C@@H](O)[C@H](C)[C@@]4(O)C[C@@H](O[C@@]5([H])C[C@H](O)[C@H](O)[C@H](C)O5)[C@H](CC)[C@@H](C)O4)OC3=O)=O)C2)C1
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,025.28 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: Li GN, Zhao XJ, Wang Z, Luo MS, Shi SN, Yan DM, Li HY, Liu JH, Yang Y, Tan JH, Zhang ZY, Chen RQ, Lai HL, Huang XY, Zhou JF, Ma D, Fang Y, Gao QL. Elaiophylin triggers paraptosis and preferentially kills ovarian cancer drug- resistant cells by inducing MAPK hyperactivation. Signal Transduct Target Ther. 2022 Sep 12;7(1):317. doi: 10.1038/s41392-022-01131-7. PMID: 36097006; PMCID: PMC9468165. 2: Ji J, Wang K, Meng X, Zhong H, Li X, Zhao H, Xie G, Xie Y, Wang X, Zhu X. Elaiophylin Inhibits Tumorigenesis of Human Lung Adenocarcinoma by Inhibiting Mitophagy via Suppression of SIRT1/Nrf2 Signaling. Cancers (Basel). 2022 Nov 25;14(23):5812. doi: 10.3390/cancers14235812. PMID: 36497294; PMCID: PMC9737501. 3: Gui M, Zhang MX, Wu WH, Sun P. Natural Occurrence, Bioactivity and Biosynthesis of Elaiophylin Analogues. Molecules. 2019 Oct 25;24(21):3840. doi: 10.3390/molecules24213840. PMID: 31731388; PMCID: PMC6864862. 4: Siddiqui FA, Vukic V, Salminen TA, Abankwa D. Elaiophylin Is a Potent Hsp90/ Cdc37 Protein Interface Inhibitor with K-Ras Nanocluster Selectivity. Biomolecules. 2021 Jun 4;11(6):836. doi: 10.3390/biom11060836. PMID: 34199986; PMCID: PMC8229862. 5: Zhu X, Zou W, Meng X, Ji J, Wang X, Shu H, Chen Y, Pan D, Wang K, Zhou F. Elaiophylin Inhibits Tumorigenesis of Human Uveal Melanoma by Suppressing Mitophagy and Inducing Oxidative Stress via Modulating SIRT1/FoxO3a Signaling. Front Oncol. 2022 Mar 21;12:788496. doi: 10.3389/fonc.2022.788496. PMID: 35387119; PMCID: PMC8978265. 6: He W, Wang W, Ma J, Zheng G, Zimin AA, Jiang W, Tian J, Lu Y. Crossregulation of rapamycin and elaiophylin biosynthesis by RapH in Streptomyces rapamycinicus. Appl Microbiol Biotechnol. 2022 Mar;106(5-6):2147-2159. doi: 10.1007/s00253-022-11847-9. Epub 2022 Feb 26. PMID: 35218390. 7: Rodrigues Dos Santos Barbosa C, Feitosa Muniz D, Silvino Pereira P, Maria de Arruda Lima S, Datiane de Morais Oliveira Tintino C, Cintia Alexandrino de Souza V, Mariana Assis da Silva J, Henrique Sousa da Costa R, Cosmo Andrade Pinheiro J, Maria Lobo Soares de Matos Y, Rose Alencar Menezes I, Gonçalves da Silva T, Manoella de Souza Lima G, Cristina Leal Balbino T, Pinto Siqueira-Júnior J, Assis Bezerra da Cunha F, Douglas Melo Coutinho H, Relison Tintino S. Evaluation of Elaiophylin extracted from Streptomyces hygroscopicus as a potential inhibitor of the NorA efflux protein in Staphylococcus aureus: An in vitro and in silico approach. Bioorg Med Chem Lett. 2021 Oct 15;50:128334. doi: 10.1016/j.bmcl.2021.128334. Epub 2021 Aug 20. PMID: 34425202. 8: Zhao X, Fang Y, Yang Y, Qin Y, Wu P, Wang T, Lai H, Meng L, Wang D, Zheng Z, Lu X, Zhang H, Gao Q, Zhou J, Ma D. Elaiophylin, a novel autophagy inhibitor, exerts antitumor activity as a single agent in ovarian cancer cells. Autophagy. 2015;11(10):1849-63. doi: 10.1080/15548627.2015.1017185. PMID: 25893854; PMCID: PMC4824600. 9: Bao R, Meng Y, Zhang H, Yang C, Li W, Zhang C, Zhang J, Sun R, Li Z, Jiang W, Zhang C, Zhang C, Yuan HX, Dang Y. Elaiophylin reduces body weight and lowers glucose levels in obese mice by activating AMPK. Cell Death Dis. 2021 Oct 20;12(11):972. doi: 10.1038/s41419-021-04264-9. PMID: 34671010; PMCID: PMC8528873. 10: Lim HN, Jang JP, Han JM, Jang JH, Ahn JS, Jung HJ. Antiangiogenic Potential of Microbial Metabolite Elaiophylin for Targeting Tumor Angiogenesis. Molecules. 2018 Mar 2;23(3):563. doi: 10.3390/molecules23030563. PMID: 29498688; PMCID: PMC6017006. 11: Xu T, Gan Q, Liu Q, Chen R, Zhen X, Zhang C, Liu J. Substrate-induced dimerization of elaiophylin glycosyltransferase reveals a novel self-activating form of glycosyltransferase for symmetric glycosylation. Acta Crystallogr D Struct Biol. 2022 Oct 1;78(Pt 10):1235-1248. doi: 10.1107/S2059798322008658. Epub 2022 Sep 27. PMID: 36189743. 12: Sheng Y, Lam PW, Shahab S, Santosa DA, Proteau PJ, Zabriskie TM, Mahmud T. Identification of Elaiophylin Skeletal Variants from the Indonesian Streptomyces sp. ICBB 9297. J Nat Prod. 2015 Nov 25;78(11):2768-75. doi: 10.1021/acs.jnatprod.5b00752. Epub 2015 Oct 28. PMID: 26510047. 13: Wang G, Zhou P, Chen X, Zhao L, Tan J, Yang Y, Fang Y, Zhou J. The novel autophagy inhibitor elaiophylin exerts antitumor activity against multiple myeloma with mutant TP53 in part through endoplasmic reticulum stress-induced apoptosis. Cancer Biol Ther. 2017 Aug 3;18(8):584-595. doi: 10.1080/15384047.2017.1345386. Epub 2017 Jul 18. PMID: 28718729; PMCID: PMC5653199. 14: Zheng J, Wang J, Wang Q, Zou H, Wang H, Zhang Z, Chen J, Wang Q, Wang P, Zhao Y, Lu J, Zhang X, Xiang S, Wang H, Lei J, Chen HW, Liu P, Liu Y, Han F, Wang J. Targeting castration-resistant prostate cancer with a novel RORγ antagonist elaiophylin. Acta Pharm Sin B. 2020 Dec;10(12):2313-2322. doi: 10.1016/j.apsb.2020.07.001. Epub 2020 Jul 12. PMID: 33354503; PMCID: PMC7745055. 15: Liu CM, Jensen L, Westley JW, Siegel D. Elaiophylin as a rumen fermentation efficiency enhancer. J Antibiot (Tokyo). 1993 Feb;46(2):350-2. doi: 10.7164/antibiotics.46.350. PMID: 8468252. 16: Cikosová M, Blazsek M, Kubis M, Gajdosíková J, Borosová G. Biotechnological preparation of the elaiophylin. Folia Microbiol (Praha). 2004;49(6):731-6. doi: 10.1007/BF02931557. PMID: 15881411. 17: Haydock SF, Mironenko T, Ghoorahoo HI, Leadlay PF. The putative elaiophylin biosynthetic gene cluster in Streptomyces sp. DSM4137 is adjacent to genes encoding adenosylcobalamin-dependent methylmalonyl CoA mutase and to genes for synthesis of cobalamin. J Biotechnol. 2004 Sep 30;113(1-3):55-68. doi: 10.1016/j.jbiotec.2004.03.022. PMID: 15380647. 18: Xu J, Wu J, Zhou D, Zhang X, Leadlay PF. Efomycine U, a new C2-asymmetric elaiophylin derivative from Streptomyces malaysiensis DSM 4137. Nat Prod Res. 2023 Jun 2:1-6. doi: 10.1080/14786419.2023.2214839. Epub ahead of print. PMID: 37265103. 19: Han Y, Tian E, Xu D, Ma M, Deng Z, Hong K. Halichoblelide D, a New Elaiophylin Derivative with Potent Cytotoxic Activity from Mangrove-Derived Streptomyces sp. 219807. Molecules. 2016 Jul 25;21(8):970. doi: 10.3390/molecules21080970. PMID: 27463707; PMCID: PMC6273579. 20: Jiang M, Yin M, Wu S, Han X, Ji K, Wen M, Lu T. GdmRIII, a TetR Family Transcriptional Regulator, Controls Geldanamycin and Elaiophylin Biosynthesis in Streptomyces autolyticus CGMCC0516. Sci Rep. 2017 Jul 6;7(1):4803. doi: 10.1038/s41598-017-05073-x. PMID: 28684749; PMCID: PMC5500506.

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