Chalcomycin

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MedKoo CAT#: 412796

CAS#: 20283-48-1

Description: Chalcomycin is a 16-membered macrolide antibiotic made by the bacterium Streptomyces bikiniensis, contains a 2,3-trans double bond and the neutral sugar D-chalcose in place of the amino sugar mycaminose found in most other 16-membered macrolides.

Chemical Structure

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Chalcomycin
CAS# 20283-48-1
Instruction

Theoretical Analysis

MedKoo Cat#: 412796
Name: Chalcomycin
CAS#: 20283-48-1
Chemical Formula: C35H56O14
Exact Mass: 700.37
Molecular Weight: 700.820
Elemental Analysis: C, 59.98; H, 8.05; O, 31.96

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 @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Chalcomycin; NSC150439; NSC-150439 NSC 150439

IUPAC/Chemical Name: (1S,2R,3R,6E,8S,9S,10S,12S,14E,16S)-12-hydroxy-2-((((2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-9-(((2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione

InChi Key: KLGADJPDTCIJLO-RVMREVNESA-N

InChi Code: InChI=1S/C35H56O14/c1-17-10-13-26(37)46-20(4)22(16-44-34-32(43-9)31(42-8)27(38)21(5)47-34)30-23(48-30)11-12-25(36)35(6,40)15-18(2)29(17)49-33-28(39)24(41-7)14-19(3)45-33/h10-13,17-24,27-34,38-40H,14-16H2,1-9H3/b12-11+,13-10+/t17-,18-,19+,20+,21+,22+,23-,24-,27+,28+,29+,30-,31+,32+,33-,34+,35-/m0/s1

SMILES Code: CO[C@H]1C[C@H](O[C@H]([C@@H]1O)O[C@H]2[C@H](C[C@](O)(C(/C=C/[C@@H]3O[C@H]3[C@@H]([C@H](OC(/C=C/[C@@H]2C)=O)C)CO[C@@H]4O[C@@H]([C@H]([C@H]([C@H]4OC)OC)O)C)=O)C)C)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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 700.82 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Dai P, Wang CX, Gao H, Wang QZ, Tang XL, Chen GD, Hong K, Hu D, Yao XS. Characterization of Methyltransferase AlmCII in Chalcomycin Biosynthesis: The First TylF Family O-Methyltransferase Works on a 4'-Deoxysugar. Chembiochem. 2017 Aug 4;18(15):1510-1517. doi: 10.1002/cbic.201700216. Epub 2017 Jun 28. PMID: 28488816.

2: Ward SL, Hu Z, Schirmer A, Reid R, Revill WP, Reeves CD, Petrakovsky OV, Dong SD, Katz L. Chalcomycin biosynthesis gene cluster from Streptomyces bikiniensis: novel features of an unusual ketolide produced through expression of the chm polyketide synthase in Streptomyces fradiae. Antimicrob Agents Chemother. 2004 Dec;48(12):4703-12. doi: 10.1128/AAC.48.12.4703-4712.2004. PMID: 15561847; PMCID: PMC529187.

3: Jiang S, Zhang L, Pei X, Deng F, Hu D, Chen G, Wang C, Hong K, Yao X, Gao AH. Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities. Mar Drugs. 2017 May 29;15(6):153. doi: 10.3390/md15060153. PMID: 28555051; PMCID: PMC5484103.

4: DeMars MD 2nd, Samora NL, Yang S, Garcia-Borràs M, Sanders JN, Houk KN, Podust LM, Sherman DH. Exploring the molecular basis for substrate specificity in homologous macrolide biosynthetic cytochromes P450. J Biol Chem. 2019 Nov 1;294(44):15947-15961. doi: 10.1074/jbc.RA119.010352. Epub 2019 Sep 5. PMID: 31488542; PMCID: PMC6827315.

5: Asolkar RN, Maskey RP, Helmke E, Laatsch H. Chalcomycin B, a new macrolide antibiotic from the marine isolate Streptomyces sp. B7064. J Antibiot (Tokyo). 2002 Oct;55(10):893-8. doi: 10.7164/antibiotics.55.893. PMID: 12523822.

6: Barger SR, Hoefler BC, Cubillos-Ruiz A, Russell WK, Russell DH, Straight PD. Imaging secondary metabolism of Streptomyces sp. Mg1 during cellular lysis and colony degradation of competing Bacillus subtilis. Antonie Van Leeuwenhoek. 2012 Oct;102(3):435-45. doi: 10.1007/s10482-012-9769-0. Epub 2012 Jul 10. PMID: 22777252.

7: Wang CX, Ding R, Jiang ST, Tang JS, Hu D, Chen GD, Lin F, Hong K, Yao XS, Gao H. Aldgamycins J-O, 16-Membered Macrolides with a Branched Octose Unit from Streptomycetes sp. and Their Antibacterial Activities. J Nat Prod. 2016 Oct 28;79(10):2446-2454. doi: 10.1021/acs.jnatprod.6b00200. Epub 2016 Sep 30. PMID: 27690254.

8: Mohimani H, Gurevich A, Shlemov A, Mikheenko A, Korobeynikov A, Cao L, Shcherbin E, Nothias LF, Dorrestein PC, Pevzner PA. Dereplication of microbial metabolites through database search of mass spectra. Nat Commun. 2018 Oct 2;9(1):4035. doi: 10.1038/s41467-018-06082-8. PMID: 30279420; PMCID: PMC6168521.

9: Tang XL, Dai P, Gao H, Wang CX, Chen GD, Hong K, Hu D, Yao XS. A Single Gene Cluster for Chalcomycins and Aldgamycins: Genetic Basis for Bifurcation of Their Biosynthesis. Chembiochem. 2016 Jul 1;17(13):1241-9. doi: 10.1002/cbic.201600118. Epub 2016 May 18. PMID: 27191535.

10: Morisaki N, Hashimoto Y, Furihata K, Yazawa K, Tamura M, Mikami Y. Glycosylative inactivation of chalcomycin and tylosin by a clinically isolated Nocardia asteroides strain. J Antibiot (Tokyo). 2001 Feb;54(2):157-65. doi: 10.7164/antibiotics.54.157. PMID: 11302489.