Aureothin | CAS# 2825-00-5 | Antifungal

MedKoo Cat#: 573549 | Name: Aureothin

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Description:

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

Aureothin is a natural nitroaryl-substituted polyketide that exhibits antitumor, antifungal, and insecticidal activities. It is a non-competitive inhibitor of NADH:ubiquinone oxidoreductase.

Chemical Structure

Aureothin

CAS#2825-00-5

Theoretical Analysis

MedKoo Cat#: 573549

Name: Aureothin

CAS#: 2825-00-5

Chemical Formula: C22H23NO6

Exact Mass: 397.1525

Molecular Weight: 397.43

Elemental Analysis: C, 66.49; H, 5.83; N, 3.52; O, 24.15

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 580.00	2 Weeks
5mg	USD 1,445.00	2 Weeks

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Related CAS #

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Synonym

Aureothin, Mycolutein, Strain 58 substance

IUPAC/Chemical Name

2-Methoxy-3,5-dimethyl-6-(tetrahydro-4-(2-methyl-3-(4-nitrophenyl)-2-propenylidene)-2-furanyl)-4H-pyran-4-one

InChi Key

OGUMLESFFBGVOO-VJDLAWOBSA-N

InChi Code

1S/C22H23NO6/c1-13(11-16-5-7-17(8-6-16)23(25)26)12-18-9-10-19(28-18)21-14(2)20(24)15(3)22(27-4)29-21/h5-8,11-12,19H,9-10H2,1-4H3/b13-11+,18-12-/t19-/m1/s1

SMILES Code

c1(oc(OC)c(C)c(=O)c1C)[C@@H]1OC(\CC1)=C\C(=C\c1ccc([N+]([O-])=O)cc1)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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 397.43 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.

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: Drissya T, Induja DK, Poornima MS, Jesmina ARS, Prabha B, Saumini M, Suresh CH, Raghu KG, Kumar BSD, Lankalapalli RS. A novel aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain. J Antibiot (Tokyo). 2022 Sep;75(9):491-497. doi: 10.1038/s41429-022-00547-1. Epub 2022 Aug 4. PMID: 35922482. 2: Busch B, Hertweck C. Evolution of metabolic diversity in polyketide-derived pyrones: using the non-colinear aureothin assembly line as a model system. Phytochemistry. 2009 Oct-Nov;70(15-16):1833-40. doi: 10.1016/j.phytochem.2009.05.022. Epub 2009 Aug 3. PMID: 19651421. 3: Henrot M, Jean A, Peixoto PA, Maddaluno J, De Paolis M. Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent. J Org Chem. 2016 Jun 17;81(12):5190-201. doi: 10.1021/acs.joc.6b00878. Epub 2016 May 27. PMID: 27213834. 4: Kim SJ, Cantrell CL, Avula B, Chen J, Schrader KK, Santo SN, Ali A, Khan IA. Streptomyces distallicus, a Potential Microbial Biolarvicide. J Agric Food Chem. 2022 Sep 14;70(36):11274-11280. doi: 10.1021/acs.jafc.2c03537. Epub 2022 Aug 30. PMID: 36040208. 5: Kang MK, Kim JH, Liu MJ, Jin CZ, Park DJ, Kim J, Sung BH, Kim CJ, Son KH. New discovery on the nematode activity of aureothin and alloaureothin isolated from endophytic bacteria Streptomyces sp. AE170020. Sci Rep. 2022 Mar 10;12(1):3947. doi: 10.1038/s41598-022-07879-w. PMID: 35273247; PMCID: PMC8913828. 6: Ueda JY, Hashimoto J, Nagai A, Nakashima T, Komaki H, Anzai K, Harayama S, Doi T, Takahashi T, Nagasawa K, Natsume T, Takagi M, Shin-ya K. New aureothin derivative, alloaureothin, from Streptomyces sp. MM23. J Antibiot (Tokyo). 2007 May;60(5):321-4. doi: 10.1038/ja.2007.41. PMID: 17551211. 7: Peng H, Ishida K, Sugimoto Y, Jenke-Kodama H, Hertweck C. Emulating evolutionary processes to morph aureothin-type modular polyketide synthases and associated oxygenases. Nat Commun. 2019 Sep 2;10(1):3918. doi: 10.1038/s41467-019-11896-1. PMID: 31477708; PMCID: PMC6718629. 8: Busch B, Ueberschaar N, Sugimoto Y, Hertweck C. Interchenar retrotransfer of aureothin intermediates in an iterative polyketide synthase module. J Am Chem Soc. 2012 Aug 1;134(30):12382-5. doi: 10.1021/ja304454r. Epub 2012 Jul 23. PMID: 22799266. 9: Herrmann A, Roesner M, Werner T, Hauck SM, Koch A, Bauer A, Schneider M, Brack-Werner R. Potent inhibition of HIV replication in primary human cells by novel synthetic polyketides inspired by Aureothin. Sci Rep. 2020 Jan 28;10(1):1326. doi: 10.1038/s41598-020-57843-9. PMID: 31992748; PMCID: PMC6987146. 10: Werneburg M, Busch B, He J, Richter ME, Xiang L, Moore BS, Roth M, Dahse HM, Hertweck C. Exploiting enzymatic promiscuity to engineer a focused library of highly selective antifungal and antiproliferative aureothin analogues. J Am Chem Soc. 2010 Aug 4;132(30):10407-13. doi: 10.1021/ja102751h. PMID: 20662518; PMCID: PMC2925430. 11: Traitcheva N, Jenke-Kodama H, He J, Dittmann E, Hertweck C. Non-colinear polyketide biosynthesis in the aureothin and neoaureothin pathways: an evolutionary perspective. Chembiochem. 2007 Oct 15;8(15):1841-9. doi: 10.1002/cbic.200700309. PMID: 17763486. 12: He J, Hertweck C. Functional analysis of the aureothin iterative type I polyketide synthase. Chembiochem. 2005 May;6(5):908-12. doi: 10.1002/cbic.200400333. PMID: 15812854. 13: Richter M, Busch B, Ishida K, Moore BS, Hertweck C. Pyran formation by an atypical CYP-mediated four-electron oxygenation-cyclization cascade in an engineered aureothin pathway. Chembiochem. 2012 Oct 15;13(15):2196-9. doi: 10.1002/cbic.201200406. Epub 2012 Sep 7. PMID: 22961965; PMCID: PMC3517090. 14: Schwartz JL, Tishler M, Arison BH, Shafer HM, Omura S. Identification of mycolutein and pulvomycin as aureothin and labilomycin respectively. J Antibiot (Tokyo). 1976 Mar;29(3):236-41. doi: 10.7164/antibiotics.29.236. PMID: 770405. 15: Sugimoto Y, Ding L, Ishida K, Hertweck C. Rational design of modular polyketide synthases: morphing the aureothin pathway into a luteoreticulin assembly line. Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1560-4. doi: 10.1002/anie.201308176. Epub 2014 Jan 8. PMID: 24402879. 16: Choi YS, Zhang H, Brunzelle JS, Nair SK, Zhao H. In vitro reconstitution and crystal structure of p-aminobenzoate N-oxygenase (AurF) involved in aureothin biosynthesis. Proc Natl Acad Sci U S A. 2008 May 13;105(19):6858-63. doi: 10.1073/pnas.0712073105. Epub 2008 May 5. PMID: 18458342; PMCID: PMC2383931. 17: Müller M, He J, Hertweck C. Dissection of the late steps in aureothin biosynthesis. Chembiochem. 2006 Jan;7(1):37-9. doi: 10.1002/cbic.200500161. PMID: 16292785. 18: Jacobsen MF, Moses JE, Adlington RM, Baldwin JE. A short total synthesis of aureothin and N-acetylaureothamine. Org Lett. 2005 Feb 17;7(4):641-4. doi: 10.1021/ol047594l. PMID: 15704914. 19: Werneburg M, Hertweck C. Chemoenzymatic total synthesis of the antiproliferative polyketide (+)-(R)-aureothin. Chembiochem. 2008 Sep 1;9(13):2064-6. doi: 10.1002/cbic.200800301. PMID: 18690656. 20: He J, Hertweck C. Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster. Chem Biol. 2003 Dec;10(12):1225-32. doi: 10.1016/j.chembiol.2003.11.009. PMID: 14700630.

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MS 154N