Chrysomycin A | CAS# 82196-88-1 | antitumor antibiotic

MedKoo Cat#: 412856 | Name: Chrysomycin A

Description:

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

Chrysomycin A is an antitumor antibiotic first isolated from Streptomyces A-419 in 1955 as a mixture with chrysomycin B

Chemical Structure

Chrysomycin A

CAS#82196-88-1

Theoretical Analysis

MedKoo Cat#: 412856

Name: Chrysomycin A

CAS#: 82196-88-1

Chemical Formula: C28H28O9

Exact Mass: 508.1733

Molecular Weight: 508.52

Elemental Analysis: C, 66.13; H, 5.55; O, 28.32

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

Chrysomycin A; NSC613946; NSC-613946; NSC 613946

IUPAC/Chemical Name

6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-3-C-methyl-beta-gulopyranosyl)-8-ethenyl-1-hydroxy-10,12-dimethoxy-

InChi Key

OMDANBMKOUVKAG-WZNMFJNZSA-N

InChi Code

InChI=1S/C28H28O9/c1-6-13-9-16-20(18(10-13)34-4)15-11-19(35-5)22-17(29)8-7-14(21(22)23(15)37-27(16)32)24-26(31)28(3,33)25(30)12(2)36-24/h6-12,24-26,29-31,33H,1H2,2-5H3/t12-,24+,25+,26+,28-/m1/s1

SMILES Code

O=C1C2=CC(C=C)=CC(OC)=C2C3=CC(OC)=C4C(O)=CC=C([C@H]5[C@@H]([C@]([C@H]([C@@H](C)O5)O)(C)O)O)C4=C3O1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 508.52 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

1: Wu F, Zhang J, Song F, Wang S, Guo H, Wei Q, Dai H, Chen X, Xia X, Liu X, Zhang L, Yu JQ, Lei X. Chrysomycin A Derivatives for the Treatment of Multi- Drug-Resistant Tuberculosis. ACS Cent Sci. 2020 Jun 24;6(6):928-938. doi: 10.1021/acscentsci.0c00122. Epub 2020 May 4. PMID: 32607440; PMCID: PMC7318084. 2: Wada SI, Sawa R, Iwanami F, Nagayoshi M, Kubota Y, Iijima K, Hayashi C, Shibuya Y, Hatano M, Igarashi M, Kawada M. Structures and biological activities of novel 4'-acetylated analogs of chrysomycins A and B. J Antibiot (Tokyo). 2017 Nov;70(11):1078-1082. doi: 10.1038/ja.2017.99. Epub 2017 Sep 6. Erratum in: J Antibiot (Tokyo). 2017 Dec;70(12 ):1150. PMID: 28874850. 3: Weiss U, Yoshihira K, Highet RJ, White RJ, Wei TT. The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A. J Antibiot (Tokyo). 1982 Sep;35(9):1194-201. doi: 10.7164/antibiotics.35.1194. PMID: 7142022. 4: Liu W, Hong B, Wang J, Lei X. New Strategies in the Efficient Total Syntheses of Polycyclic Natural Products. Acc Chem Res. 2020 Nov 17;53(11):2569-2586. doi: 10.1021/acs.accounts.0c00531. Epub 2020 Nov 2. PMID: 33136373. 5: Carter GT, Fantini AA, James JC, Borders DB, White RJ. Biosynthesis of chrysomycins A and B. Origin of the chromophore. J Antibiot (Tokyo). 1985 Feb;38(2):242-8. doi: 10.7164/antibiotics.38.242. PMID: 3997669. 6: STRELITZ F, FLON H, ASHESHOV IN. Chrysomycin: a new antibiotic substance for bacterial viruses. J Bacteriol. 1955 Mar;69(3):280-3. doi: 10.1128/JB.69.3.280-283.1955. PMID: 14367272; PMCID: PMC357526. 7: Kharel MK, Nybo SE, Shepherd MD, Rohr J. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters. Chembiochem. 2010 Mar 1;11(4):523-32. doi: 10.1002/cbic.200900673. PMID: 20140934; PMCID: PMC2879346. 8: Wei TT, Byrne KM, Warnick-Pickle D, Greenstein M. Studies on the mechanism of actin of gilvocarcin V and chrysomycin A. J Antibiot (Tokyo). 1982 Apr;35(4):545-8. doi: 10.7164/antibiotics.35.545. PMID: 7096212. 9: Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, Rohr J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21. PMID: 22186970. 10: Matson JA, Rose WC, Bush JA, Myllymaki R, Bradner WT, Doyle TW. Antitumor activity of chrysomycins M and V. J Antibiot (Tokyo). 1989 Sep;42(9):1446-8. doi: 10.7164/antibiotics.42.1446. PMID: 2793599.

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