MedKoo Cat#: 585319 | Name: Kalafungin

Description:

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

Kalafungin antimicrobial agent that is inhibitory in vitro against a variety of pathogenic fungi, yeasts, protozoa, gram-positive bacteria, and, to a lesser extent, gram-negative bacteria.

Chemical Structure

Kalafungin
Kalafungin
CAS#11048-15-0

Theoretical Analysis

MedKoo Cat#: 585319

Name: Kalafungin

CAS#: 11048-15-0

Chemical Formula: C16H12O6

Exact Mass: 300.0634

Molecular Weight: 300.27

Elemental Analysis: C, 64.00; H, 4.03; O, 31.97

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
Kalafungin; Antibiotic U-19,718; U 19718; U19718; U-19718
IUPAC/Chemical Name
4-hydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
InChi Key
XUWPJKDMEZSVTP-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O6/c1-6-11-13(16-9(21-6)5-10(18)22-16)14(19)7-3-2-4-8(17)12(7)15(11)20/h2-4,6,9,16-17H,5H2,1H3
SMILES Code
O=C(C1=C2C=CC=C1O)C3=C(C4OC(CC4OC3C)=O)C2=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 300.27 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: Kakinuma S, Takada Y, Ikeda H, Tanaka H, Omura S, Hopwood DA. Cloning of large DNA fragments, which hybridize with actinorhodin biosynthesis genes, from kalafungin and nanaomycin A methyl ester producers and identification of genes for kalafungin biosynthesis of the kalafungin producer. J Antibiot (Tokyo). 1991 Sep;44(9):995-1005. PubMed PMID: 1938623. 2: Kakinuma S, Ikeda H, Omura S, Hopwood DA. Biosynthesis of kalafungin in Streptomyces tanashiensis. J Antibiot (Tokyo). 1990 Apr;43(4):391-6. PubMed PMID: 2351613. 3: Lü J, He Q, Huang L, Cai X, Guo W, He J, Zhang L, Li A. Accumulation of a bioactive benzoisochromanequinone compound kalafungin by a wild type antitumor-medermycin-producing streptomycete strain. PLoS One. 2015 Feb 19;10(2):e0117690. doi: 10.1371/journal.pone.0117690. eCollection 2015. PubMed PMID: 25695632; PubMed Central PMCID: PMC4335000. 4: Kakinuma S, Ikeda H, Takada Y, Tanaka H, Hopwood DA, Omura S. Production of the new antibiotic tetrahydrokalafungin by transformants of the kalafungin producer Streptomyces tanashiensis. J Antibiot (Tokyo). 1995 Jun;48(6):484-7. PubMed PMID: 7622434. 5: Fernandes RA, Chavan VP, Mulay SV, Manchoju A. A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin. J Org Chem. 2012 Nov 16;77(22):10455-60. doi: 10.1021/jo3019939. Epub 2012 Oct 31. PubMed PMID: 23088749. 6: Johnson LE, Dietz A. Kalafungin, a new antibiotic produced by Streptomyces tanashiensis strain Kala. Appl Microbiol. 1968 Dec;16(12):1815-21. PubMed PMID: 5726156; PubMed Central PMCID: PMC547777. 7: Karwowski JP, Jackson M, Theriault RJ, Prokop JF, Maus ML, Hansen CF, Hensey DM. Arizonins, a new complex of antibiotics related to kalafungin. I. Taxonomy of the producing culture, fermentation and biological activity. J Antibiot (Tokyo). 1988 Sep;41(9):1205-11. PubMed PMID: 3182401. 8: Hoeksema H, Krueger WC. Kalafungin. II. Chemical transformations and the absolute configuration. J Antibiot (Tokyo). 1976 Jul;29(7):704-9. PubMed PMID: 956056. 9: Hochlowski JE, Brill GM, Andres WW, Spanton SG, McAlpine JB. Arizonins, a new complex of antibiotics related to kalafungin. II. Isolation and characterization. J Antibiot (Tokyo). 1987 Apr;40(4):401-7. PubMed PMID: 3583911. 10: Tsujibo H, Sakamoto T, Miyamoto K, Kusano G, Ogura M, Hasegawa T, Inamori Y. Isolation of cytotoxic substance, kalafungin from an alkalophilic actinomycete, Nocardiopsis dassonvillei subsp. prasina. Chem Pharm Bull (Tokyo). 1990 Aug;38(8):2299-300. PubMed PMID: 2279296. 11: Bergy ME. Kalafungin, a new broad spectrum antibiotic. Isolation and characterization. J Antibiot (Tokyo). 1968 Jul;21(7):454-7. PubMed PMID: 4303501. 12: Eid CN, Shim J, Bikker J, Lin M. Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin. J Org Chem. 2009 Jan 2;74(1):423-6. doi: 10.1021/jo801945n. PubMed PMID: 19053617. 13: Rosenfeld EL, Laubach HE. Effects of sugars on the anthelmintic activity of kalafungin. J Parasitol. 1986 Oct;72(5):770-2. PubMed PMID: 3806325. 14: Tatsuta K, Akimoto K, Annaka M, Ohno Y, Kinoshita M. Enantiodivergent total syntheses of (-)-nanaomycin D and its enantiomer, (+)-kalafungin. J Antibiot (Tokyo). 1985 May;38(5):680-2. PubMed PMID: 4019313. 15: Oja T, San Martin Galindo P, Taguchi T, Manner S, Vuorela PM, Ichinose K, Metsä-Ketelä M, Fallarero A. Effective Antibiofilm Polyketides against Staphylococcus aureus from the Pyranonaphthoquinone Biosynthetic Pathways of Streptomyces Species. Antimicrob Agents Chemother. 2015 Oct;59(10):6046-52. doi: 10.1128/AAC.00991-15. Epub 2015 Jul 20. PubMed PMID: 26195520; PubMed Central PMCID: PMC4576117. 16: Tahlan K, Ahn SK, Sing A, Bodnaruk TD, Willems AR, Davidson AR, Nodwell JR. Initiation of actinorhodin export in Streptomyces coelicolor. Mol Microbiol. 2007 Feb;63(4):951-61. PubMed PMID: 17338074. 17: Valton J, Fontecave M, Douki T, Kendrew SG, Nivière V. An aromatic hydroxylation reaction catalyzed by a two-component FMN-dependent Monooxygenase. The ActVA-ActVB system from Streptomyces coelicolor. J Biol Chem. 2006 Jan 6;281(1):27-35. Epub 2005 Nov 2. PubMed PMID: 16267053. 18: Kakinuma S, Ikeda H, Tanaka H, Omura S. Isolation of restriction-reduced mutants from Streptomyces. Agric Biol Chem. 1990 Oct;54(10):2611-7. PubMed PMID: 1368599. 19: Taguchi T, Okamoto S, Hasegawa K, Ichinose K. Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin. Chembiochem. 2011 Dec 16;12(18):2767-73. doi: 10.1002/cbic.201100571. Epub 2011 Nov 15. PubMed PMID: 22086671. 20: Okabe T, Nomoto K, Funabashi H, Okuda S, Suzuki H, Tanaka N. Lactoquinomycin, a novel anticancer antibiotic. II. Physico-chemical properties and structure assignment. J Antibiot (Tokyo). 1985 Oct;38(10):1333-6. PubMed PMID: 3840792.