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MedKoo Cat#: 573760 | Name: Asukamycin
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Description:

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

Asukamycin is polyketide isolated from the S. nodosus subspecies asukaensis that demonstrates a broad range of antibiotic functions. It has been shown to inhibit growth of various tumor cell lines by activating caspases 8 and 3.

Chemical Structure

Asukamycin
Asukamycin
CAS#61116-33-4

Theoretical Analysis

MedKoo Cat#: 573760

Name: Asukamycin

CAS#: 61116-33-4

Chemical Formula: C31H34N2O7

Exact Mass: 546.2366

Molecular Weight: 546.62

Elemental Analysis: C, 68.12; H, 6.27; N, 5.12; O, 20.49

Price and Availability

Size Price Availability Quantity
500µg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
AM 1042, AM1042, AM-1042, Asukamycin A
IUPAC/Chemical Name
(2E,4E,6E)-7-cyclohexyl-N-((1S,5S,6R)-5-hydroxy-5-((1E,3E,5E)-7-((2-hydroxy-5-oxocyclopent-1-en-1-yl)amino)-7-oxohepta-1,3,5-trien-1-yl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)hepta-2,4,6-trienamide
InChi Key
SSHVAUUEPNULMP-JHWDTTIQSA-N
InChi Code
InChI=1S/C31H34N2O7/c34-23-17-18-24(35)27(23)33-26(37)16-10-3-4-11-19-31(39)20-22(28(38)29-30(31)40-29)32-25(36)15-9-2-1-6-12-21-13-7-5-8-14-21/h1-4,6,9-12,15-16,19-21,29-30,34,39H,5,7-8,13-14,17-18H2,(H,32,36)(H,33,37)/b2-1+,4-3+,12-6+,15-9+,16-10+,19-11+/t29-,30-,31+/m1/s1
SMILES Code
O=C1[C@@H]2[C@@H](O2)[C@@](/C=C/C=C/C=C/C(NC3=C(O)CCC3=O)=O)(O)C=C1NC(/C=C/C=C/C=C/C4CCCCC4)=O
Appearance
Solid powder
Purity
>95% (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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 546.62 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: Yan X, Zhang J, Tan H, Liu Z, Jiang K, Tian W, Zheng M, Lin Z, Deng Z, Qu X. A Pair of Atypical KAS III Homologues with Initiation and Elongation Functions Program the Polyketide Biosynthesis in Asukamycin. Angew Chem Int Ed Engl. 2022 May 2;61(19):e202200879. doi: 10.1002/anie.202200879. Epub 2022 Mar 10. PMID: 35218125. 2: Rui Z, Petrícková K, Skanta F, Pospísil S, Yang Y, Chen CY, Tsai SF, Floss HG, Petrícek M, Yu TW. Biochemical and genetic insights into asukamycin biosynthesis. J Biol Chem. 2010 Aug 6;285(32):24915-24. doi: 10.1074/jbc.M110.128850. Epub 2010 Jun 3. PMID: 20522559; PMCID: PMC2915727. 3: Xie P, Sheng Y, Ito T, Mahmud T. Transcriptional regulation and increased production of asukamycin in engineered Streptomyces nodosus subsp. asukaensis strains. Appl Microbiol Biotechnol. 2012 Oct;96(2):451-60. doi: 10.1007/s00253-012-4084-2. Epub 2012 May 5. PMID: 22555913. 4: Shipley PR, Donnelly CC, Le CH, Bernauer AD, Klegeris A. Antitumor activity of asukamycin, a secondary metabolite from the actinomycete bacterium Streptomyces nodosus subspecies asukaensis. Int J Mol Med. 2009 Nov;24(5):711-5. doi: 10.3892/ijmm_00000283. PMID: 19787206. 5: Omura S, Kitao C, Tanaka H, Oiwa R, Takahashi Y. A new antibiotic,, asukamycin, produced by Streptomyces. J Antibiot (Tokyo). 1976 Sep;29(9):876-81. doi: 10.7164/antibiotics.29.876. PMID: 993129. 6: Hu Y, Floss HG. Further studies on the biosynthesis of the manumycin-type antibiotic, asukamycin, and the chemical synthesis of protoasukamycin. J Am Chem Soc. 2004 Mar 31;126(12):3837-44. doi: 10.1021/ja039336+. PMID: 15038738. 7: Pospíšil S, Petříčková K, Sedmera P, Halada P, Olšovská J, Petříček M. Effect of starter unit availability on the spectrum of manumycin-type metabolites produced by Streptomyces nodosus ssp. asukaensis. J Appl Microbiol. 2011 Nov;111(5):1116-28. doi: 10.1111/j.1365-2672.2011.05132.x. Epub 2011 Sep 8. PMID: 21854515. 8: Petrícek M, Petrícková K, Havlícek L, Felsberg J. Occurrence of two 5-aminolevulinate biosynthetic pathways in Streptomyces nodosus subsp. asukaensis is linked with the production of asukamycin. J Bacteriol. 2006 Jul;188(14):5113-23. doi: 10.1128/JB.01919-05. PMID: 16816183; PMCID: PMC1539946. 9: Brodasky TF, Stroman DW, Dietz A, Mizsak S. U-56,407, a new antibiotic related to asukamycin: isolation and characterization. J Antibiot (Tokyo). 1983 Aug;36(8):950-6. doi: 10.7164/antibiotics.36.950. PMID: 6630064. 10: Floss HG, Keller PJ, Beale JM. Studies on the biosynthesis of antibiotics. J Nat Prod. 1986 Nov-Dec;49(6):957-70. doi: 10.1021/np50048a001. PMID: 3553432. 11: Hu D, Gao C, Sun C, Jin T, Fan G, Mok KM, Lee SM. Genome-guided and mass spectrometry investigation of natural products produced by a potential new actinobacterial strain isolated from a mangrove ecosystem in Futian, Shenzhen, China. Sci Rep. 2019 Jan 29;9(1):823. doi: 10.1038/s41598-018-37475-w. PMID: 30696899; PMCID: PMC6351551. 12: Ito T. [Biosynthetic study of actinomycetes-metabolites for creating novel analogs]. Yakugaku Zasshi. 2013;133(9):1007-15. Japanese. doi: 10.1248/yakushi.13-00175. PMID: 23995809. 13: Silva LR, da Silva-Júnior EF. Inhibiting the "Undruggable" RAS/Farnesyltransferase (FTase) Cancer Target by Manumycin-related Natural Products. Curr Med Chem. 2022;29(2):189-211. doi: 10.2174/0929867328666210315123848. PMID: 33719954. 14: Rui Z, Sandy M, Jung B, Zhang W. Tandem enzymatic oxygenations in biosynthesis of epoxyquinone pharmacophore of manumycin-type metabolites. Chem Biol. 2013 Jul 25;20(7):879-87. doi: 10.1016/j.chembiol.2013.05.006. PMID: 23890006. 15: Petříčková K, Pospíšil S, Kuzma M, Tylová T, Jágr M, Tomek P, Chroňáková A, Brabcová E, Anděra L, Krištůfek V, Petříček M. Biosynthesis of colabomycin E, a new manumycin-family metabolite, involves an unusual chain-length factor. Chembiochem. 2014 Jun 16;15(9):1334-45. doi: 10.1002/cbic.201400068. Epub 2014 May 18. PMID: 24838618. 16: Hrdý J, Súkeníková L, Petrásková P, Novotná O, Kahoun D, Petříček M, Chroňáková A, Petříčková K. Inhibition of Pro-Inflammatory Cytokines by Metabolites of Streptomycetes-A Potential Alternative to Current Anti- Inflammatory Drugs? Microorganisms. 2020 Apr 25;8(5):621. doi: 10.3390/microorganisms8050621. PMID: 32344935; PMCID: PMC7284804. 17: Hu Y, Floss HG. New type II manumycins produced by Streptomyces nodosus ssp. asukaensis and their biosynthesis. J Antibiot (Tokyo). 2001 Apr;54(4):340-8. doi: 10.7164/antibiotics.54.340. PMID: 11426658. 18: Isobe Y, Okumura M, McGregor LM, Brittain SM, Jones MD, Liang X, White R, Forrester W, McKenna JM, Tallarico JA, Schirle M, Maimone TJ, Nomura DK. Manumycin polyketides act as molecular glues between UBR7 and P53. Nat Chem Biol. 2020 Nov;16(11):1189-1198. doi: 10.1038/s41589-020-0557-2. Epub 2020 Jun 22. PMID: 32572277; PMCID: PMC7572527. 19: Wipf P, Coish PDG. Total Synthesis of (±)-Nisamycin. J Org Chem. 1999 Jul 9;64(14):5053-5061. doi: 10.1021/jo990413m. PMID: 34237846. 20: Bai L. Tandem modifications of an epoxyquinone C7N pharmacophore. Chem Biol. 2013 Jul 25;20(7):859-60. doi: 10.1016/j.chembiol.2013.07.003. PMID: 23890003.

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