Candicidin D

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

MedKoo CAT#: 598741

CAS#: 39372-30-0

Description: Candicidin D is an antifungal compound obtained from Streptomyces griseus.

Chemical Structure

Candicidin D
CAS# 39372-30-0

Theoretical Analysis

MedKoo Cat#: 598741
Name: Candicidin D
CAS#: 39372-30-0
Chemical Formula: C59H84N2O18
Exact Mass: 1108.5719
Molecular Weight: 1109.31
Elemental Analysis: C, 63.88; H, 7.63; N, 2.53; O, 25.96

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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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 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1109.31 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.

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

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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.