Eburicone | CAS#118492-82-3 | antifungal agent

MedKoo Cat#: 598328 | Name: Eburicone

Description:

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

Eburicone is an antifungal agent.

Chemical Structure

Eburicone

CAS#118492-82-3

Theoretical Analysis

MedKoo Cat#: 598328

Name: Eburicone

CAS#: 118492-82-3

Chemical Formula: C31H50O

Exact Mass: 438.3862

Molecular Weight: 438.74

Elemental Analysis: C, 84.87; H, 11.49; O, 3.65

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Eburicone;

IUPAC/Chemical Name

(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-1,2,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key

HCVPIOTWCPCBAF-YQGXAETFSA-N

InChi Code

InChI=1S/C31H50O/c1-20(2)21(3)10-11-22(4)23-14-18-31(9)25-12-13-26-28(5,6)27(32)16-17-29(26,7)24(25)15-19-30(23,31)8/h20,22-23,26H,3,10-19H2,1-2,4-9H3/t22-,23-,26+,29-,30-,31+/m1/s1

SMILES Code

CC1(C)C(CC[C@]2(C)C3=C([C@@]4(CC[C@@H]([C@]4(CC3)C)[C@H](C)CCC(C(C)C)=C)C)CC[C@@]12[H])=O

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 438.74 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: Price CL, Warrilow AG, Parker JE, Mullins JG, Nes WD, Kelly DE, Kelly SL. Novel Substrate Specificity and Temperature-Sensitive Activity of Mycosphaerella graminicola CYP51 Supported by the Native NADPH Cytochrome P450 Reductase. Appl Environ Microbiol. 2015 May 15;81(10):3379-86. doi: 10.1128/AEM.03965-14. Epub 2015 Mar 6. PubMed PMID: 25746994; PubMed Central PMCID: PMC4407231. 2: Bean TP, Cools HJ, Lucas JA, Hawkins ND, Ward JL, Shaw MW, Fraaije BA. Sterol content analysis suggests altered eburicol 14alpha-demethylase (CYP51) activity in isolates of Mycosphaerella graminicola adapted to azole fungicides. FEMS Microbiol Lett. 2009 Jun;296(2):266-73. doi: 10.1111/j.1574-6968.2009.01645.x. Epub 2009 May 8. PubMed PMID: 19459949. 3: van Nistelrooy JG, van den Brink JM, van Kan JA, van Gorcom RF, de Waard MA. Isolation and molecular characterisation of the gene encoding eburicol 14 alpha-demethylase (cYP51) from Penicillium italicum. Mol Gen Genet. 1996 Apr 10;250(6):725-33. PubMed PMID: 8628233. 4: van den Brink HJ, van Nistelrooy HJ, de Waard MA, van den Hondel CA, van Gorcom RF. Increased resistance to 14 alpha-demethylase inhibitors (DMIs) in Aspergillus niger by coexpression of the Penicillium italicum eburicol 14 alpha-demethylase (cyp51) and the A. niger cytochrome P450 reductase (cprA) genes. J Biotechnol. 1996 Aug 20;49(1-3):13-8. PubMed PMID: 8879162. 5: Subden RE, Safe L, Morris DC, Brown RG, Safe S. Eburicol, lichesterol, ergosterol, and obtusifoliol from polyene antibiotic-resistant mutants of Candida albicans. Can J Microbiol. 1977 Jun;23(6):751-4. PubMed PMID: 326362. 6: Délye C, Laigret F, Corio-Costet MF. Cloning and sequence analysis of the eburicol 14alpha-demethylase gene of the obligate biotrophic grape powdery mildew fungus. Gene. 1997 Aug 11;195(1):29-33. PubMed PMID: 9300816. 7: Warrilow AG, Parker JE, Price CL, Nes WD, Garvey EP, Hoekstra WJ, Schotzinger RJ, Kelly DE, Kelly SL. The Investigational Drug VT-1129 Is a Highly Potent Inhibitor of Cryptococcus Species CYP51 but Only Weakly Inhibits the Human Enzyme. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4530-8. doi: 10.1128/AAC.00349-16. Print 2016 Aug. PubMed PMID: 27161631; PubMed Central PMCID: PMC4958158. 8: Délye C, Bousset L, Corio-Costet MF. PCR cloning and detection of point mutations in the eburicol 14alpha-demethylase (CYP51) gene from Erysiphe graminis f. sp. hordei, a "recalcitrant" fungus. Curr Genet. 1998 Dec;34(5):399-403. PubMed PMID: 9871123. 9: Cools HJ, Parker JE, Kelly DE, Lucas JA, Fraaije BA, Kelly SL. Heterologous expression of mutated eburicol 14alpha-demethylase (CYP51) proteins of Mycosphaerella graminicola to assess effects on azole fungicide sensitivity and intrinsic protein function. Appl Environ Microbiol. 2010 May;76(9):2866-72. doi: 10.1128/AEM.02158-09. Epub 2010 Mar 19. PubMed PMID: 20305029; PubMed Central PMCID: PMC2863451. 10: Vanden Bossche H, Marichal P, Le Jeune L, Coene MC, Gorrens J, Cools W. Effects of itraconazole on cytochrome P-450-dependent sterol 14 alpha-demethylation and reduction of 3-ketosteroids in Cryptococcus neoformans. Antimicrob Agents Chemother. 1993 Oct;37(10):2101-5. PubMed PMID: 8257130; PubMed Central PMCID: PMC192235. 11: Harmouch N, Coulon J, Bonaly R. Identification of 24-methylene-24,25-dihydrolanosterol as a precursor of ergosterol in the yeasts Schizosaccharomyces pombe and Schizosaccharomyces octosporus. FEMS Microbiol Lett. 1995 Dec 15;134(2-3):147-52. PubMed PMID: 8586261. 12: Warrilow AG, Melo N, Martel CM, Parker JE, Nes WD, Kelly SL, Kelly DE. Expression, purification, and characterization of Aspergillus fumigatus sterol 14-alpha demethylase (CYP51) isoenzymes A and B. Antimicrob Agents Chemother. 2010 Oct;54(10):4225-34. doi: 10.1128/AAC.00316-10. Epub 2010 Jul 26. PubMed PMID: 20660663; PubMed Central PMCID: PMC2944604. 13: Fan J, Urban M, Parker JE, Brewer HC, Kelly SL, Hammond-Kosack KE, Fraaije BA, Liu X, Cools HJ. Characterization of the sterol 14α-demethylases of Fusarium graminearum identifies a novel genus-specific CYP51 function. New Phytol. 2013 May;198(3):821-35. doi: 10.1111/nph.12193. Epub 2013 Feb 27. PubMed PMID: 23442154. 14: Nes WD, Zhou W, Ganapathy K, Liu J, Vatsyayan R, Chamala S, Hernandez K, Miranda M. Sterol 24-C-methyltransferase: an enzymatic target for the disruption of ergosterol biosynthesis and homeostasis in Cryptococcus neoformans. Arch Biochem Biophys. 2009 Jan 15;481(2):210-8. doi: 10.1016/j.abb.2008.11.003. Epub 2008 Nov 8. PubMed PMID: 19014901. 15: Parker JE, Warrilow AG, Cools HJ, Martel CM, Nes WD, Fraaije BA, Lucas JA, Kelly DE, Kelly SL. Mechanism of binding of prothioconazole to Mycosphaerella graminicola CYP51 differs from that of other azole antifungals. Appl Environ Microbiol. 2011 Feb;77(4):1460-5. doi: 10.1128/AEM.01332-10. Epub 2010 Dec 17. PubMed PMID: 21169436; PubMed Central PMCID: PMC3067226. 16: Hargrove TY, Wawrzak Z, Lamb DC, Guengerich FP, Lepesheva GI. Structure-Functional Characterization of Cytochrome P450 Sterol 14α-Demethylase (CYP51B) from Aspergillus fumigatus and Molecular Basis for the Development of Antifungal Drugs. J Biol Chem. 2015 Sep 25;290(39):23916-34. doi: 10.1074/jbc.M115.677310. Epub 2015 Aug 12. PubMed PMID: 26269599; PubMed Central PMCID: PMC4583043. 17: Warrilow AG, Parker JE, Price CL, Nes WD, Kelly SL, Kelly DE. In Vitro Biochemical Study of CYP51-Mediated Azole Resistance in Aspergillus fumigatus. Antimicrob Agents Chemother. 2015 Dec;59(12):7771-8. doi: 10.1128/AAC.01806-15. Epub 2015 Oct 12. PubMed PMID: 26459890; PubMed Central PMCID: PMC4649140. 18: Zhang J, Wang ZM, Liu KC, He QX, Qi YD, Zhang BG, Liu HT, Xiao PG. [Chemical constituents of Kadsura oblongifolia and evaluation of their toxicity]. Yao Xue Xue Bao. 2014 Sep;49(9):1296-303. Chinese. PubMed PMID: 25518329. 19: Zhou X, Zhou J, Tian H, Yuan Y. Dynamic lipidomic insights into the adaptive responses of Saccharomyces cerevisiae to the repeated vacuum fermentation. OMICS. 2010 Oct;14(5):563-74. doi: 10.1089/omi.2010.0016. PubMed PMID: 20955009. 20: Warrilow AG, Price CL, Parker JE, Rolley NJ, Smyrniotis CJ, Hughes DD, Thoss V, Nes WD, Kelly DE, Holman TR, Kelly SL. Azole Antifungal Sensitivity of Sterol 14α-Demethylase (CYP51) and CYP5218 from Malassezia globosa. Sci Rep. 2016 Jun 13;6:27690. doi: 10.1038/srep27690. PubMed PMID: 27291783; PubMed Central PMCID: PMC4904373.