Ilicicolin A | CAS#22581-06-2 | cytochrome bc1 reductase inhibitor

MedKoo Cat#: 599067 | Name: Ilicicolin A

Description:

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

Ilicicolin A is a cytochrome bc1 reductase inhibitor broad spectrum antifungal agent.

Chemical Structure

Ilicicolin A

CAS#22581-06-2

Theoretical Analysis

MedKoo Cat#: 599067

Name: Ilicicolin A

CAS#: 22581-06-2

Chemical Formula: C23H31ClO3

Exact Mass: 390.1962

Molecular Weight: 390.94

Elemental Analysis: C, 70.66; H, 7.99; Cl, 9.07; O, 12.28

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

Ilicicolin A; LL-Z 1272-alpha; LL Z 1272-alpha; LLZ 1272-alpha;

IUPAC/Chemical Name

3-chloro-4,6-dihydroxy-2-methyl-5-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)benzaldehyde

InChi Key

MHWOMRMBQGSTFS-JTCWOHKRSA-N

InChi Code

InChI=1S/C23H31ClO3/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-19-22(26)20(14-25)18(5)21(24)23(19)27/h8,10,12,14,26-27H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+

SMILES Code

O=CC1=C(O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C(O)C(Cl)=C1C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 390.94 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: Singh SB, Liu W, Li X, Chen T, Shafiee A, Card D, Abruzzo G, Flattery A, Gill C, Thompson JR, Rosenbach M, Dreikorn S, Hornak V, Meinz M, Kurtz M, Kelly R, Onishi JC. Antifungal spectrum, in vivo efficacy, and structure-activity relationship of ilicicolin h. ACS Med Chem Lett. 2012 Sep 7;3(10):814-7. doi: 10.1021/ml300173e. eCollection 2012 Oct 11. PubMed PMID: 24900384; PubMed Central PMCID: PMC4025731. 2: Singh SB, Liu W, Li X, Chen T, Shafiee A, Dreikorn S, Hornak V, Meinz M, Onishi JC. Structure-activity relationship of cytochrome bc1 reductase inhibitor broad spectrum antifungal ilicicolin H. Bioorg Med Chem Lett. 2013 May 15;23(10):3018-22. doi: 10.1016/j.bmcl.2013.03.023. Epub 2013 Mar 15. PubMed PMID: 23562597. 3: Ding MG, di Rago JP, Trumpower BL. Investigating the Qn site of the cytochrome bc1 complex in Saccharomyces cerevisiae with mutants resistant to ilicicolin H, a novel Qn site inhibitor. J Biol Chem. 2006 Nov 24;281(47):36036-43. Epub 2006 Sep 20. PubMed PMID: 16987808. 4: Gutierrez-Cirlos EB, Merbitz-Zahradnik T, Trumpower BL. Inhibition of the yeast cytochrome bc1 complex by ilicicolin H, a novel inhibitor that acts at the Qn site of the bc1 complex. J Biol Chem. 2004 Mar 5;279(10):8708-14. Epub 2003 Dec 10. PubMed PMID: 14670947. 5: Gutiérrez M, Theoduloz C, Rodríguez J, Lolas M, Schmeda-Hirschmann G. Bioactive metabolites from the fungus Nectria galligena, the main apple canker agent in Chile. J Agric Food Chem. 2005 Oct 5;53(20):7701-8. PubMed PMID: 16190620. 6: Covian R, Trumpower BL. Ilicicolin Inhibition and Binding at Center N of the Dimeric Cytochrome bc1 Complex Reveal Electron Transfer and Regulatory Interactions between Monomers. J Biol Chem. 2009 Mar 27;284(13):8614-20. doi: 10.1074/jbc.M808914200. Epub 2009 Jan 27. PubMed PMID: 19176478; PubMed Central PMCID: PMC2659220. 7: Rotsaert FA, Ding MG, Trumpower BL. Differential efficacy of inhibition of mitochondrial and bacterial cytochrome bc1 complexes by center N inhibitors antimycin, ilicicolin H and funiculosin. Biochim Biophys Acta. 2008 Feb;1777(2):211-9. Epub 2007 Nov 1. PubMed PMID: 18022381; PubMed Central PMCID: PMC2677292. 8: Shen W, Ren X, Zhu J, Xu Y, Lin J, Li Y, Zhao F, Zheng H, Li R, Cui X, Zhang X, Lu X, Zheng Z. Discovery of a new structural class of competitive hDHODH inhibitors with in vitro and in vivo anti-inflammatory, immunosuppressive effects. Eur J Pharmacol. 2016 Nov 15;791:205-212. doi: 10.1016/j.ejphar.2016.09.004. Epub 2016 Sep 3. PubMed PMID: 27597161. 9: Wu B, Oesker V, Wiese J, Malien S, Schmaljohann R, Imhoff JF. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347. Mar Drugs. 2014 Apr 1;12(4):1924-38. doi: 10.3390/md12041924. PubMed PMID: 24694571; PubMed Central PMCID: PMC4012445. 10: Ding MG, Butler CA, Saracco SA, Fox TD, Godard F, di Rago JP, Trumpower BL. Introduction of cytochrome b mutations in Saccharomyces cerevisiae by a method that allows selection for both functional and non-functional cytochrome b proteins. Biochim Biophys Acta. 2008 Sep;1777(9):1147-56. doi: 10.1016/j.bbabio.2008.04.029. Epub 2008 Apr 27. PubMed PMID: 18498758; PubMed Central PMCID: PMC2601669. 11: Kildgaard S, Subko K, Phillips E, Goidts V, de la Cruz M, Díaz C, Gotfredsen CH, Andersen B, Frisvad JC, Nielsen KF, Larsen TO. A Dereplication and Bioguided Discovery Approach to Reveal New Compounds from a Marine-Derived Fungus Stilbella fimetaria. Mar Drugs. 2017 Aug 13;15(8). pii: E253. doi: 10.3390/md15080253. PubMed PMID: 28805711; PubMed Central PMCID: PMC5577607. 12: Covian R, Zwicker K, Rotsaert FA, Trumpower BL. Asymmetric and redox-specific binding of quinone and quinol at center N of the dimeric yeast cytochrome bc1 complex. Consequences for semiquinone stabilization. J Biol Chem. 2007 Aug 17;282(33):24198-208. Epub 2007 Jun 21. PubMed PMID: 17584742.