Chrysomycin A

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

MedKoo CAT#: 412856

CAS#: 82196-88-1

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

Chemical Structure

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Chrysomycin A
CAS# 82196-88-1
Instruction

Theoretical Analysis

MedKoo Cat#: 412856
Name: Chrysomycin A
CAS#: 82196-88-1
Chemical Formula: C28H28O9
Exact Mass: 508.17
Molecular Weight: 508.520
Elemental Analysis: C, 66.13; H, 5.55; O, 28.32

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: 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:

Biological target:
In vitro activity:
In vivo activity:

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.

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: 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.