Echinocandin B | CAS# 54651-05-7 | Antibiotic

MedKoo Cat#: 571102 | Name: Echinocandin B

Description:

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

Echinocandin B is a cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. echinulatus with specific anti-yeast activity. It inhibits beta-1,3-glucan synthesis and thus attacks the cell wall of fungi.

Chemical Structure

Echinocandin B

CAS#54651-05-7

Theoretical Analysis

MedKoo Cat#: 571102

Name: Echinocandin B

CAS#: 54651-05-7

Chemical Formula: C52H81N7O16

Exact Mass: 1059.5740

Molecular Weight: 1060.25

Elemental Analysis: C, 58.91; H, 7.70; N, 9.25; O, 24.14

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 #

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Synonym

Echinocandin B; NSC 287461; A30912A; A 30912A; A-30912A; A22082; A 22082; A-22082

IUPAC/Chemical Name

(9Z,12Z)-N-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6,20-bis((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)octadeca-9,12-dienamide

InChi Key

FAUOJMHVEYMQQG-HVYQDZECSA-N

InChi Code

1S/C52H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h9-10,12-13,21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-8,11,14-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)/b10-9-,13-12-/t29-,30+,31+,34+,35-,36-,37+,39-,40-,41-,42-,43-,44-,45-,48+/m0/s1

SMILES Code

CCCCC\C=C/C\C=C/CCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@@H](O)CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)c4ccc(O)cc4)[C@@H](C)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

>2 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 1,060.25 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

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PubMed PMID: 25541471. 4: Elefanti A, Mouton JW, Verweij PE, Tsakris A, Zerva L, Meletiadis J. Amphotericin B- and voriconazole-echinocandin combinations against Aspergillus spp.: Effect of serum on inhibitory and fungicidal interactions. Antimicrob Agents Chemother. 2013 Oct;57(10):4656-63. doi: 10.1128/AAC.00597-13. Epub 2013 Jul 15. PubMed PMID: 23856768; PubMed Central PMCID: PMC3811418. 5: Hüttel W, Youssar L, Grüning BA, Günther S, Hugentobler KG. Echinocandin B biosynthesis: a biosynthetic cluster from Aspergillus nidulans NRRL 8112 and reassembly of the subclusters Ecd and Hty from Aspergillus pachycristatus NRRL 11440 reveals a single coherent gene cluster. BMC Genomics. 2016 Aug 8;17:570. doi: 10.1186/s12864-016-2885-x. PubMed PMID: 27502607; PubMed Central PMCID: PMC4977696. 6: Niu K, Hu Y, Mao J, Zou S, Zheng Y. [Effect of microparticles on echinocandin B production by Aspergillus nidulans]. Sheng Wu Gong Cheng Xue Bao. 2015 Jul;31(7):1082-8. Chinese. PubMed PMID: 26647583. 7: Zou SP, Zhong W, Xia CJ, Gu YN, Niu K, Zheng YG, Shen YC. Mutagenesis breeding of high echinocandin B producing strain and further titer improvement with culture medium optimization. Bioprocess Biosyst Eng. 2015 Oct;38(10):1845-54. doi: 10.1007/s00449-015-1425-4. Epub 2015 Jun 20. PubMed PMID: 26091897. 8: Emri T, Majoros L, Tóth V, Pócsi I. Echinocandins: production and applications. Appl Microbiol Biotechnol. 2013 Apr;97(8):3267-84. doi: 10.1007/s00253-013-4761-9. Epub 2013 Mar 6. Review. PubMed PMID: 23463246. 9: Cacho RA, Jiang W, Chooi YH, Walsh CT, Tang Y. Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella rugulosa NRRL 11440. J Am Chem Soc. 2012 Oct 10;134(40):16781-90. doi: 10.1021/ja307220z. Epub 2012 Oct 1. PubMed PMID: 22998630; PubMed Central PMCID: PMC3482383. 10: Tóth V, Nagy CT, Pócsi I, Emri T. The echinocandin B producer fungus Aspergillus nidulans var. roseus ATCC 58397 does not possess innate resistance against its lipopeptide antimycotic. Appl Microbiol Biotechnol. 2012 Jul;95(1):113-22. doi: 10.1007/s00253-012-4027-y. Epub 2012 May 4. PubMed PMID: 22555909. 11: Kuhn DM, George T, Chandra J, Mukherjee PK, Ghannoum MA. Antifungal susceptibility of Candida biofilms: unique efficacy of amphotericin B lipid formulations and echinocandins. Antimicrob Agents Chemother. 2002 Jun;46(6):1773-80. PubMed PMID: 12019089; PubMed Central PMCID: PMC127206. 12: Julius JM, Gaikwad A, Lowry A, Lewis RE, Lozano RD, Dalrymple JL, Coleman RL, Smith JA. Defining the role of echinocandin catechol functional groups in the development of secondary hepatocellular carcinoma. J Antimicrob Chemother. 2012 Feb;67(2):422-9. doi: 10.1093/jac/dkr494. Epub 2011 Nov 30. PubMed PMID: 22129592. 13: Debono M, Abbott BJ, Fukuda DS, Barnhart M, Willard KE, Molloy RM, Michel KH, Turner JR, Butler TF, Hunt AH. 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J Antibiot (Tokyo). 1989 Mar;42(3):382-8. PubMed PMID: 2708131. 19: Morrison VA. The role of caspofungin and the echinocandins in the antifungal armamentarium. Curr Opin Investig Drugs. 2002 Oct;3(10):1432-6. Review. PubMed PMID: 12431014. 20: Hodges RL, Hodges DW, Goggans K, Xuei X, Skatrud P, McGilvray D. Genetic modification of an echinocandin B-producing strain of Aspergillus nidulans to produce mutants blocked in sterigmatocystin biosynthesis. J Ind Microbiol. 1994 Nov;13(6):372-81. PubMed PMID: 7765669.