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MedKoo Cat#: 413048 | Name: Cladosporin

Description:

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

Cladosporin is an antifungal metabolite from Cladosporium cladosporioides; toxic, minor metabolite of Aspersillus flavus; inhibits tRNA synthetase in Plasmodium falciparum.

Chemical Structure

Cladosporin
Cladosporin
CAS#35818-31-6

Theoretical Analysis

MedKoo Cat#: 413048

Name: Cladosporin

CAS#: 35818-31-6

Chemical Formula: C16H20O5

Exact Mass: 292.1311

Molecular Weight: 292.33

Elemental Analysis: C, 65.74; H, 6.90; O, 27.36

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 #
No Data
Synonym
Cladosporin; Asperentin
IUPAC/Chemical Name
1H-2-Benzopyran-1-one, 3,4-dihydro-6,8-dihydroxy-3-((tetrahydro-6-methyl-2H-pyran-2-yl)methyl)-, (2R-(2-alpha(R*),6-beta))-
InChi Key
WOMKDMUZNBFXKG-JIMOISOXSA-N
InChi Code
InChI=1S/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3/t9-,12+,13-/m1/s1
SMILES Code
O=C1C2=C(O)C=C(O)C=C2C[C@H](C[C@@H]3CCC[C@@H](C)O3)O1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 292.33 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: Wang X, Wedge DE, Cutler SJ. Chemical and Biological Study of Cladosporin, an Antimicrobial Inhibitor: A Review. Nat Prod Commun. 2016 Oct;11(10):1595-1600. PMID: 30549627. 2: Fredenhagen A, Schroer K, Schröder H, Hoepfner D, Ligibel M, Porchet Zemp L, Radoch C, Freund E, Meishammer A. Cladosporin Derivatives Obtained by Biotransformation Provide Guidance for the Focused Derivatization of this Antimalarial Lead Compound. Chembiochem. 2019 Mar 1;20(5):650-654. doi: 10.1002/cbic.201800588. Epub 2018 Dec 11. PMID: 30347507. 3: Rusch M, Thevenon A, Hoepfner D, Aust T, Studer C, Patoor M, Rollin P, Livendahl M, Ranieri B, Schmitt E, Spanka C, Gademann K, Bouchez LC. Design and Synthesis of Metabolically Stable tRNA Synthetase Inhibitors Derived from Cladosporin. Chembiochem. 2019 Mar 1;20(5):644-649. doi: 10.1002/cbic.201800587. Epub 2019 Feb 4. PMID: 30462880. 4: Cochrane RV, Sanichar R, Lambkin GR, Reiz B, Xu W, Tang Y, Vederas JC. Production of New Cladosporin Analogues by Reconstitution of the Polyketide Synthases Responsible for the Biosynthesis of this Antimalarial Agent. Angew Chem Int Ed Engl. 2016 Jan 11;55(2):664-8. doi: 10.1002/anie.201509345. Epub 2015 Nov 24. PMID: 26783060; PMCID: PMC4906947. 5: Baragaña B, Forte B, Choi R, Nakazawa Hewitt S, Bueren-Calabuig JA, Pisco JP, Peet C, Dranow DM, Robinson DA, Jansen C, Norcross NR, Vinayak S, Anderson M, Brooks CF, Cooper CA, Damerow S, Delves M, Dowers K, Duffy J, Edwards TE, Hallyburton I, Horst BG, Hulverson MA, Ferguson L, Jiménez-Díaz MB, Jumani RS, Lorimer DD, Love MS, Maher S, Matthews H, McNamara CW, Miller P, O'Neill S, Ojo KK, Osuna-Cabello M, Pinto E, Post J, Riley J, Rottmann M, Sanz LM, Scullion P, Sharma A, Shepherd SM, Shishikura Y, Simeons FRC, Stebbins EE, Stojanovski L, Straschil U, Tamaki FK, Tamjar J, Torrie LS, Vantaux A, Witkowski B, Wittlin S, Yogavel M, Zuccotto F, Angulo-Barturen I, Sinden R, Baum J, Gamo FJ, Mäser P, Kyle DE, Winzeler EA, Myler PJ, Wyatt PG, Floyd D, Matthews D, Sharma A, Striepen B, Huston CD, Gray DW, Fairlamb AH, Pisliakov AV, Walpole C, Read KD, Van Voorhis WC, Gilbert IH. Lysyl-tRNA synthetase as a drug target in malaria and cryptosporidiosis. Proc Natl Acad Sci U S A. 2019 Apr 2;116(14):7015-7020. doi: 10.1073/pnas.1814685116. Epub 2019 Mar 20. PMID: 30894487; PMCID: PMC6452685. 6: Das P, Babbar P, Malhotra N, Sharma M, Jachak GR, Gonnade RG, Shanmugam D, Harlos K, Yogavel M, Sharma A, Reddy DS. Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite. J Med Chem. 2018 Jul 12;61(13):5664-5678. doi: 10.1021/acs.jmedchem.8b00565. Epub 2018 Jun 4. PMID: 29779382. 7: Khan S, Sharma A, Belrhali H, Yogavel M, Sharma A. Structural basis of malaria parasite lysyl-tRNA synthetase inhibition by cladosporin. J Struct Funct Genomics. 2014 Jun;15(2):63-71. doi: 10.1007/s10969-014-9182-1. Epub 2014 Jun 17. PMID: 24935905. 8: Chhibber-Goel J, Sharma A. Side chain rotameric changes and backbone dynamics enable specific cladosporin binding in Plasmodium falciparum lysyl-tRNA synthetase. Proteins. 2019 Sep;87(9):730-737. doi: 10.1002/prot.25699. Epub 2019 May 9. PMID: 31017332. 9: Zheng H, Zhao C, Fang B, Jing P, Yang J, Xie X, She X. Asymmetric total synthesis of cladosporin and isocladosporin. J Org Chem. 2012 Jul 6;77(13):5656-63. doi: 10.1021/jo300805n. Epub 2012 Jun 11. PMID: 22663064. 10: Scott PM, Van Walbeek W, MacLean WM. Cladosporin, a new antifungal metabolite from Cladosporium cladosporioides. J Antibiot (Tokyo). 1971 Nov;24(11):747-55. doi: 10.7164/antibiotics.24.747. PMID: 5169000.