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MedKoo Cat#: 461565 | Name: Rustmicin

Description:

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

Rustmicin is a 14-membered macrolide identified as an inhibitor of plant pathogenic fungi.

Chemical Structure

Rustmicin
Rustmicin
CAS#100227-57-4

Theoretical Analysis

MedKoo Cat#: 461565

Name: Rustmicin

CAS#: 100227-57-4

Chemical Formula: C21H32O6

Exact Mass: 380.2199

Molecular Weight: 380.48

Elemental Analysis: C, 66.29; H, 8.48; O, 25.23

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 #
No Data
Synonym
Rustmicin; Galbonolide;
IUPAC/Chemical Name
(3R,5S,7E,9S,12E,14S)-14-ethyl-5-hydroxy-5-(hydroxymethyl)-7-methoxy-3,9,13-trimethyl-11-methyleneoxacyclotetradeca-7,12-diene-2,4-dione
InChi Key
WOFFENQLRMDHKE-AWJXAEAHSA-N
InChi Code
InChI=1S/C21H32O6/c1-7-18-15(4)9-13(2)8-14(3)10-17(26-6)11-21(25,12-22)19(23)16(5)20(24)27-18/h9-10,14,16,18,22,25H,2,7-8,11-12H2,1,3-6H3/b15-9+,17-10+/t14-,16+,18-,21-/m0/s1
SMILES Code
CC[C@H](O1)/C(C)=C/C(C[C@H](C)/C=C(OC)\C[C@](O)(CO)C([C@@H](C)C1=O)=O)=C
Appearance
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
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 380.48 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: Mandala SM, Thornton RA, Milligan J, Rosenbach M, Garcia-Calvo M, Bull HG, Harris G, Abruzzo GK, Flattery AM, Gill CJ, Bartizal K, Dreikorn S, Kurtz MB. Rustmicin, a potent antifungal agent, inhibits sphingolipid synthesis at inositol phosphoceramide synthase. J Biol Chem. 1998 Jun 12;273(24):14942-9. PubMed PMID: 9614099. 2: Sigmund JM, Hirsch CF. Fermentation studies of rustmicin production by a Micromonospora sp. J Antibiot (Tokyo). 1998 Sep;51(9):829-36. PubMed PMID: 9820233. 3: Figueiredo JM, Dias WB, Mendonça-Previato L, Previato JO, Heise N. Characterization of the inositol phosphorylceramide synthase activity from Trypanosoma cruzi. Biochem J. 2005 Apr 15;387(Pt 2):519-29. PubMed PMID: 15569002; PubMed Central PMCID: PMC1134981. 4: Liu C, Zhu J, Li Y, Zhang J, Lu C, Wang H, Shen Y. In vitro reconstitution of a PKS pathway for the biosynthesis of galbonolides in Streptomyces sp. LZ35. Chembiochem. 2015 Apr 13;16(6):998-1007. doi: 10.1002/cbic.201500017. Epub 2015 Mar 3. PubMed PMID: 25735238. 5: Harris GH, Shafiee A, Cabello MA, Curotto JE, Genilloud O, Göklen KE, Kurtz MB, Rosenbach M, Salmon PM, Thornton RA, Zink DL, Mandala SM. Inhibition of fungal sphingolipid biosynthesis by rustmicin, galbonolide B and their new 21-hydroxy analogs. J Antibiot (Tokyo). 1998 Sep;51(9):837-44. PubMed PMID: 9820234. 6: Liu C, Zhang J, Lu C, Shen Y. Heterologous expression of galbonolide biosynthetic genes in Streptomyces coelicolor. Antonie Van Leeuwenhoek. 2015 May;107(5):1359-66. doi: 10.1007/s10482-015-0415-5. Epub 2015 Mar 4. PubMed PMID: 25735435. 7: Takatsu T, Nakayama H, Shimazu A, Furihata K, Ikeda K, Furihata K, Seto H, Otake N. Rustmicin, a new macrolide antibiotic active against wheat stem rust fungus. J Antibiot (Tokyo). 1985 Dec;38(12):1806-9. PubMed PMID: 3841538. 8: Mandala SM, Harris GH. Isolation and characterization of novel inhibitors of sphingolipid synthesis: australifungin, viridiofungins, rustmicin, and khafrefungin. Methods Enzymol. 2000;311:335-48. PubMed PMID: 10563338. 9: Nakayama H, Hanamura T, Abe Y, Shimazu A, Furihata K, Ikeda K, Furihata K, Seto H, Otake N. Structures of neorustmicins B, C and D new congeners of rustmicin and neorustmicin A. J Antibiot (Tokyo). 1986 Jul;39(7):1016-20. PubMed PMID: 3759645. 10: Kim HJ, Karki S, Kwon SY, Park SH, Nahm BH, Kim YK, Kwon HJ. A single module type I polyketide synthase directs de novo macrolactone biogenesis during galbonolide biosynthesis in Streptomyces galbus. J Biol Chem. 2014 Dec 12;289(50):34557-68. doi: 10.1074/jbc.M114.602334. Epub 2014 Oct 21. PubMed PMID: 25336658; PubMed Central PMCID: PMC4263863. 11: Aeed PA, Young CL, Nagiec MM, Elhammer AP. Inhibition of inositol phosphorylceramide synthase by the cyclic peptide aureobasidin A. Antimicrob Agents Chemother. 2009 Feb;53(2):496-504. doi: 10.1128/AAC.00633-08. Epub 2008 Dec 1. PubMed PMID: 19047657; PubMed Central PMCID: PMC2630602. 12: Sakoh H, Sugimoto Y, Imamura H, Sakuraba S, Jona H, Bamba-Nagano R, Yamada K, Hashizume T, Morishima H. Novel galbonolide derivatives as IPC synthase inhibitors: design, synthesis and in vitro antifungal activities. Bioorg Med Chem Lett. 2004 Jan 5;14(1):143-5. PubMed PMID: 14684316. 13: Sakoh H, Sakuraba S, Sugimoto Y, Imamura H, Jona H, Yamada K, Bamba-Nagano R, Hashizume T, Morishima H. Synthesis and antifungal activity of novel 14-membered benzomacrolides, as galbonolide analogues. Chem Pharm Bull (Tokyo). 2004 Jan;52(1):163-5. PubMed PMID: 14709890. 14: Achenbach H, Mühlenfeld A, Fauth U, Zähner H. The galbonolides. Novel, powerful antifungal macrolides from Streptomyces galbus ssp. eurythermus. Ann N Y Acad Sci. 1988;544:128-40. PubMed PMID: 3214064. 15: Bromley PE, Li YO, Murphy SM, Sumner CM, Lynch DV. Complex sphingolipid synthesis in plants: characterization of inositolphosphorylceramide synthase activity in bean microsomes. Arch Biochem Biophys. 2003 Sep 15;417(2):219-26. PubMed PMID: 12941304. 16: Karki S, Kwon SY, Yoo HG, Suh JW, Park SH, Kwon HJ. The methoxymalonyl-acyl carrier protein biosynthesis locus and the nearby gene with the beta-ketoacyl synthase domain are involved in the biosynthesis of galbonolides in Streptomyces galbus, but these loci are separate from the modular polyketide synthase gene cluster. FEMS Microbiol Lett. 2010 Sep 1;310(1):69-75. doi: 10.1111/j.1574-6968.2010.02048.x. Epub 2010 Jun 24. PubMed PMID: 20662933. 17: Sugimoto Y, Sakoh H, Yamada K. IPC synthase as a useful target for antifungal drugs. Curr Drug Targets Infect Disord. 2004 Dec;4(4):311-22. Review. PubMed PMID: 15578972. 18: Fauth U, Zähner H, Mühlenfeld A, Achenbach H. Galbonolides A and B--two non-glycosidic antifungal macrolides. J Antibiot (Tokyo). 1986 Dec;39(12):1760-4. PubMed PMID: 3818448. 19: Sakoh H, Jona H, Sugimoto Y, Imamura H, Sakuraba S, Yamada K, Morishima H. Synthesis of a key intermediate of novel galbonolide analogues via efficient construction of a conjugated diene system. Chem Pharm Bull (Tokyo). 2004 Aug;52(8):992-4. PubMed PMID: 15304999.