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MedKoo Cat#: 461331 | Name: Rimocidin

Description:

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

Rimocidin is a macrolide antifungal agent isolated from Streptomyces rimosus.

Chemical Structure

Rimocidin
Rimocidin
CAS#1393-12-0

Theoretical Analysis

MedKoo Cat#: 461331

Name: Rimocidin

CAS#: 1393-12-0

Chemical Formula: C39H61NO14

Exact Mass: 767.4092

Molecular Weight: 767.91

Elemental Analysis: C, 61.00; H, 8.01; N, 1.82; O, 29.17

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
Rimocidin; Rimocidine;
IUPAC/Chemical Name
(1R,3S,9R,10S,13R,15E,17Z,19E,21E,23R,25R,26R,27S)-23-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-ethyl-1,3,9,27-tetrahydroxy-7,11-dioxo-13-propyl-12,29-dioxabicyclo[23.3.1]nonacosa-15,17,19,21-tetraene-26-carboxylic acid
InChi Key
AWGBZRVEGDNLDZ-UEPXWEONSA-N
InChi Code
InChI=1S/C39H61NO14/c1-4-14-26-17-11-9-7-6-8-10-12-18-27(53-38-35(46)33(40)34(45)23(3)51-38)20-31-32(36(47)48)30(44)22-39(50,54-31)21-25(42)16-13-15-24(41)19-29(43)28(5-2)37(49)52-26/h6-12,18,23,25-35,38,42-46,50H,4-5,13-17,19-22,40H2,1-3H3,(H,47,48)/b7-6-,10-8+,11-9+,18-12+/t23-,25+,26-,27+,28+,29-,30+,31-,32-,33+,34-,35+,38+,39-/m1/s1
SMILES Code
O[C@@H]1[C@H](O[C@H]2/C=C/C=C/C=C\C=C\C[C@@H](CCC)OC([C@@H](CC)[C@@H](CC(CCC[C@@H](C[C@]3(O)C[C@H](O)[C@@H](C(O)=O)[C@@H](C2)O3)O)=O)O)=O)O[C@H](C)[C@@H](O)[C@@H]1N
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 767.91 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: Escudero L, Al-Refai M, Nieto C, Laatsch H, Malpartida F, Seco EM. New Rimocidin/CE-108 Derivatives Obtained by a Crotonyl-CoA Carboxylase/Reductase Gene Disruption in Streptomyces diastaticus var. 108: Substrates for the Polyene Carboxamide Synthase PcsA. PLoS One. 2015 Aug 18;10(8):e0135891. doi: 10.1371/journal.pone.0135891. eCollection 2015. PubMed PMID: 26284936; PubMed Central PMCID: PMC4540446. 2: Jeon BJ, Kim JD, Han JW, Kim BS. Antifungal activity of rimocidin and a new rimocidin derivative BU16 produced by Streptomyces mauvecolor BU16 and their effects on pepper anthracnose. J Appl Microbiol. 2016 May;120(5):1219-28. doi: 10.1111/jam.13071. Epub 2016 Mar 17. PubMed PMID: 26808253. 3: Phornphisutthimas S, Sudtachat N, Bunyoo C, Chotewutmontri P, Panijpan B, Thamchaipenet A. Development of an intergeneric conjugal transfer system for rimocidin-producing Streptomyces rimosus. Lett Appl Microbiol. 2010 May;50(5):530-6. doi: 10.1111/j.1472-765X.2010.02835.x. Epub 2010 Mar 17. PubMed PMID: 20337930. 4: DAVISSON JW, TANNER FW Jr, FINLAY AC, SOLOMONS IA. Rimocidin, a new antibiotic. Antibiot Chemother (Northfield). 1951 Aug;1(5):289-90. PubMed PMID: 24541674. 5: Sowiński P, Pawlak J, Borowski E, Gariboldi P. Stereostructure of Rimocidin. J Antibiot (Tokyo). 1995 Nov;48(11):1288-91. PubMed PMID: 8557570. 6: Falkowski L, Golik J, Zielinski J, Borowski E. The structure of rimocidin. J Antibiot (Tokyo). 1976 Feb;29(2):197-8. PubMed PMID: 931803. 7: Seco EM, Pérez-Zúñiga FJ, Rolón MS, Malpartida F. Starter unit choice determines the production of two tetraene macrolides, rimocidin and CE-108, in Streptomyces diastaticus var. 108. Chem Biol. 2004 Mar;11(3):357-66. PubMed PMID: 15123265. 8: Smith AB 3rd, Pitram SM, Fuertes MJ. (+)-Rimocidin synthetic studies. Construction of an advanced C(1-18) polyol fragment. Org Lett. 2003 Jul 24;5(15):2751-4. PubMed PMID: 12868906. 9: Packard GK, Hu Y, Vescovi A, Rychnovsky SD. Synthesis of rimocidinolide methyl ester, the aglycone of (+)-rimocidin. Angew Chem Int Ed Engl. 2004 May 17;43(21):2822-6. PubMed PMID: 15150759. 10: Smith AB 3rd, Foley MA, Dong S, Orbin A. (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton. J Org Chem. 2009 Aug 21;74(16):5987-6001. doi: 10.1021/jo900765p. PubMed PMID: 19621880; PubMed Central PMCID: PMC2891182. 11: Seco EM, Fotso S, Laatsch H, Malpartida F. A tailoring activity is responsible for generating polyene amide derivatives in Streptomyces diastaticus var. 108. Chem Biol. 2005 Oct;12(10):1093-101. PubMed PMID: 16242652. 12: SENECA H, KANE JH, ROCKENBACH J. Protozoicidal properties of rimocidin. Antibiot Chemother (Northfield). 1952 Aug;2(8):435-7. PubMed PMID: 24542067. 13: Falkowski L, Zieliński J, Golik J, Bylec E, Borowski E. The structure of rimocidin: mass spectrometric analysis of derivatives of the antibiotic. J Antibiot (Tokyo). 1978 Aug;31(8):742-9. PubMed PMID: 690007. 14: OKAMI Y, UTAHARA R, NAKAMURA S, UMEZAWA H. Studies on antibiotic actinomycetes. IX. On Streptomyces producing a new antifungal substance mediocidin and antifungal substances of fungicidin-rimocidin-chromin group, eurocidin group and trichomycin-ascosin-candicidin group. J Antibiot (Tokyo). 1954 May;7(3):98-103. PubMed PMID: 13192035. 15: Pandey RC, Rinehart KL Jr. Polyene antibiotics. VIII. The structure of rimocidin. J Antibiot (Tokyo). 1977 Feb;30(2):146-57. PubMed PMID: 849916. 16: Cope AC, Burrows EP, Derieg ME, Moon S, Wirth WD. Rimocidin. I. Carbon skeleton, partial structure, and absolute configuration at C-27. J Am Chem Soc. 1965 Dec 5;87(23):5452-60. PubMed PMID: 5844822. 17: Seco EM, Miranzo D, Nieto C, Malpartida F. The pcsA gene from Streptomyces diastaticus var. 108 encodes a polyene carboxamide synthase with broad substrate specificity for polyene amides biosynthesis. Appl Microbiol Biotechnol. 2010 Feb;85(6):1797-807. doi: 10.1007/s00253-009-2193-3. Epub 2009 Aug 26. PubMed PMID: 19707755. 18: Pérez-Zúñiga FJ, Seco EM, Cuesta T, Degenhardt F, Rohr J, Vallín C, Iznaga Y, Pérez ME, González L, Malpartida F. CE-108, a new macrolide tetraene antibiotic. J Antibiot (Tokyo). 2004 Mar;57(3):197-204. PubMed PMID: 15152805. 19: Heia S, Borgos SE, Sletta H, Escudero L, Seco EM, Malpartida F, Ellingsen TE, Zotchev SB. Initiation of polyene macrolide biosynthesis: interplay between polyketide synthase domains and modules as revealed via domain swapping, mutagenesis, and heterologous complementation. Appl Environ Microbiol. 2011 Oct;77(19):6982-90. doi: 10.1128/AEM.05781-11. Epub 2011 Aug 5. PubMed PMID: 21821762; PubMed Central PMCID: PMC3187094. 20: Lee MY, Kim HY, Lee S, Kim JG, Suh JW, Lee CH. Metabolomics-Based Chemotaxonomic Classification of Streptomyces spp. and Its Correlation with Antibacterial Activity. J Microbiol Biotechnol. 2015 Aug;25(8):1265-74. doi: 10.4014/jmb.1503.03005. PubMed PMID: 25876602.

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