WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H598741
CAS#: 39372-30-0
Description: Candicidin D is an antifungal compound obtained from Streptomyces griseus.
Hodoodo Cat#: H598741
Name: Candicidin D
CAS#: 39372-30-0
Chemical Formula: C59H84N2O18
Exact Mass: 1,108.57
Molecular Weight: 1,109.310
Elemental Analysis: C, 63.88; H, 7.63; N, 2.53; O, 25.96
This product is not in stock, which may be available by custom synthesis.
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Synonym: Candicidin D; LIA-0704; LIA 0704; LIA0704; Levorin A2; Candicidin D1;
IUPAC/Chemical Name: (10R,12S,14S,18S,19S,20S,22R,23E,25E,27Z,29Z,31E,33E,35E,37S,38R)-22-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-38-((2S,4S,5S)-7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl)-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxooxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
InChi Key: OPGSFDUODIJJGF-XHQWTUNZSA-N
InChi Code: InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-47(78-59-56(74)54(61)55(73)38(4)77-59)33-51(71)53(58(75)76)50(70)31-46(67)30-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)32-52(72)79-57(35)37(3)26-36(2)48(68)34-49(69)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-45,47-48,50-51,53-57,59,64-66,68,70-71,73-74H,17,19-20,26-34,60-61H2,1-4H3,(H,75,76)/b6-5-,9-7+,10-8-,13-11+,14-12+,18-15+,21-16+/t35-,36-,37-,38+,43-,44-,45-,47-,48-,50-,51-,53+,54-,55+,56-,57-,59-/m0/s1
SMILES Code: C[C@H]([C@H](CC(c1ccc(N)cc1)=O)O)C[C@@H]([C@H]2OC(CC(CCCC(C[C@@H](C[C@@H](C[C@@H](CC(C[C@@H]([C@@H](C(O)=O)[C@H](C[C@H](/C=C/C=C/C=C\C=C/C=C/C=C/C=C/[C@@H]2C)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@@H]3O)N)O)C)O)O)=O)O)O)O)=O)=O)=O)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: 2934.99.03.00
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,109.31 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Szwarc K, Szczeblewski P, Sowiński P, Borowski E, Pawlak J. The stereostructure of candicidin D. J Antibiot (Tokyo). 2015 Aug;68(8):504-10. doi: 10.1038/ja.2015.17. Epub 2015 Feb 25. PubMed PMID: 25712395.
2: Lei X, Kong L, Zhang C, You D, Deng Z. [Function of transporter genes fscTI and fscTII in the biosynthetic cluster of candicidin/FR-008]. Wei Sheng Wu Xue Bao. 2012 Dec 4;52(12):1458-66. Chinese. PubMed PMID: 23457795.
3: Zhang P, Zhao Z, Li H, Chen XL, Deng Z, Bai L, Pang X. Production of the antibiotic FR-008/candicidin in Streptomyces sp. FR-008 is co-regulated by two regulators, FscRI and FscRIV, from different transcription factor families. Microbiology. 2015 Mar;161(Pt 3):539-52. doi: 10.1099/mic.0.000033. Epub 2015 Jan 9. PubMed PMID: 25575546.
4: Lei X, Kong L, Zhang C, Liu Q, Yao F, Zhang W, Deng Z, You D. In vivo investigation of the substrate recognition capability and activity affecting amino acid residues of glycosyltransferase FscMI in the biosynthesis of candicidin. Mol Biosyst. 2013 Mar;9(3):422-30. doi: 10.1039/c2mb25464f. Epub 2013 Jan 17. PubMed PMID: 23324745.
5: Martín JF, Aparicio JF. Enzymology of the polyenes pimaricin and candicidin biosynthesis. Methods Enzymol. 2009;459:215-42. doi: 10.1016/S0076-6879(09)04610-2. PubMed PMID: 19362642.
6: Gil JA, Campelo-Diez AB. Candicidin biosynthesis in Streptomyces griseus. Appl Microbiol Biotechnol. 2003 Feb;60(6):633-42. Epub 2002 Dec 18. Review. PubMed PMID: 12664141.
7: Haeder S, Wirth R, Herz H, Spiteller D. Candicidin-producing Streptomyces support leaf-cutting ants to protect their fungus garden against the pathogenic fungus Escovopsis. Proc Natl Acad Sci U S A. 2009 Mar 24;106(12):4742-6. doi: 10.1073/pnas.0812082106. Epub 2009 Mar 6. PubMed PMID: 19270078; PubMed Central PMCID: PMC2660719.
8: Jørgensen H, Fjaervik E, Hakvåg S, Bruheim P, Bredholt H, Klinkenberg G, Ellingsen TE, Zotchev SB. Candicidin biosynthesis gene cluster is widely distributed among Streptomyces spp. isolated from the sediments and the neuston layer of the Trondheim fjord, Norway. Appl Environ Microbiol. 2009 May;75(10):3296-303. doi: 10.1128/AEM.02730-08. Epub 2009 Mar 13. PubMed PMID: 19286787; PubMed Central PMCID: PMC2681660.
9: Cybulska B, Borowski E, Prigent Y, Gary-Bobo CM. Cation permeability induced by two aromatic heptaenes, vacidin A and candicidin D on phospholipid unilamellar vesicles. J Antibiot (Tokyo). 1981 Jul;34(7):884-91. PubMed PMID: 7197269.
10: Chen S, Mao X, Shen Y, Zhou Y, Li J, Wang L, Tao X, Yang L, Wang Y, Zhou X, Deng Z, Wei D. Tailoring the P450 monooxygenase gene for FR-008/candicidin biosynthesis. Appl Environ Microbiol. 2009 Mar;75(6):1778-81. doi: 10.1128/AEM.00859-08. Epub 2009 Jan 9. PubMed PMID: 19139241; PubMed Central PMCID: PMC2655452.
11: Liu DM, McDaniel LE, Schaffner CP. Factors affecting the production of candicidin. Antimicrob Agents Chemother. 1975 Feb;7(2):196-202. PubMed PMID: 806261; PubMed Central PMCID: PMC429103.
12: Martin JF, Mcdaniel LE. Specific inhibition of candicidin biosynthesis by the lipogenic inhibitor cerulenin. Biochim Biophys Acta. 1975 Dec 5;411(2):186-94. PubMed PMID: 811262.
13: Seipke RF, Barke J, Brearley C, Hill L, Yu DW, Goss RJ, Hutchings MI. A single Streptomyces symbiont makes multiple antifungals to support the fungus farming ant Acromyrmex octospinosus. PLoS One. 2011;6(8):e22028. doi: 10.1371/journal.pone.0022028. Epub 2011 Aug 3. PubMed PMID: 21857911; PubMed Central PMCID: PMC3153929.
14: Szwarc K, Szczeblewski P, Sowiński P, Borowski E, Pawlak J. The structure, including stereochemistry, of levorin A1. Magn Reson Chem. 2015 Jun;53(6):479-84. doi: 10.1002/mrc.4229. Epub 2015 Mar 13. PubMed PMID: 25773336.
15: Asturias JA, Martín JF, Liras P. Biosynthesis and phosphate control of candicidin by Streptomyces acrimycini JI2236: effect of amplification of the pabAB gene. J Ind Microbiol. 1994 May;13(3):183-9. PubMed PMID: 7764844.
16: Madsen PO, Dørflinger T, Frimodt-Møller PC, Jensen KM. Candicidin in treatment of benign prostatic hypertrophy. J Urol. 1984 Dec;132(6):1235-8. PubMed PMID: 6209428.
17: Martín JF, Naharro G, Liras P, Villanueva JR. Isolation of mutants deregulated in phosphate control of candicidin biosynthesis. J Antibiot (Tokyo). 1979 Jun;32(6):600-6. PubMed PMID: 112091.
18: Singhal AK, Mosbach EH, Schaffner CP. Effect of candicidin on cholesterol and bile acid metabolism in the rat. Lipids. 1981 Jun;16(6):423-6. PubMed PMID: 7266266.
19: Kivinen S, Tarkkila T, Laakso L, Laakso K. Short-term topical treatment of vulvovaginal candidiasis with the combination of 5-fluorocytosine and candicidin. Curr Med Res Opin. 1979;6(2):88-92. PubMed PMID: 467093.
20: Chen S, Huang X, Zhou X, Bai L, He J, Jeong KJ, Lee SY, Deng Z. Organizational and mutational analysis of a complete FR-008/candicidin gene cluster encoding a structurally related polyene complex. Chem Biol. 2003 Nov;10(11):1065-76. PubMed PMID: 14652074.
