Synonym
Echinosporin; XK-213; XK 213; XK213.
IUPAC/Chemical Name
1,5-(Epoxymethano)cyclopenta(c)pyran-3-carboxamide, 1,4a,5,7a-tetrahydro-5-hydroxy-8-oxo-, (1S-(1-alpha,4a-beta,5-beta,7a-beta))-
InChi Key
OXSZHYWOGQJUST-OFCCZVAHSA-N
InChi Code
InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)/t4-,5+,8-,10+/m1/s1
SMILES Code
O=C(C1=C[C@@]([C@@](C(O2)=O)(O)C=C3)([H])[C@]3([H])[C@]2([H])O1)N
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
223.18
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: Dame ZT, Islam MT, Helmke E, von Tiedemann A, Laatsch H. Oligomycins and pamamycin homologs impair motility and induce lysis of zoospores of the grapevine downy mildew pathogen, Plasmopara viticola. FEMS Microbiol Lett. 2016 Aug;363(16). pii: fnw167. doi: 10.1093/femsle/fnw167. Epub 2016 Jun 27. PubMed PMID: 27354061.
2: Lankapalli AR, Kannabiran K. Interaction of marine Streptomyces compounds with selected cancer drug target proteins by in silico molecular docking studies. Interdiscip Sci. 2013 Mar;5(1):37-44. doi: 10.1007/s12539-013-0146-0. Epub 2013 Apr 19. PubMed PMID: 23605638.
3: Flasz JT, Hale KJ. A new stereocontrolled synthetic route to (-)-echinosporin from D-glucose via Padwa allenylsulfone [3 + 2]-anionic cycloadditive elimination. Org Lett. 2012 Jun 15;14(12):3024-7. doi: 10.1021/ol301090v. Epub 2012 May 30. PubMed PMID: 22646909.
4: Cui CB, Liu HB, Gu JY, Gu QQ, Cai B, Zhang DY, Zhu TJ. Echinosporins as new cell cycle inhibitors and apoptosis inducers from marine-derived Streptomyces albogriseolus. Fitoterapia. 2007 Apr;78(3):238-40. Epub 2007 Feb 6. PubMed PMID: 17376609.
5: Morimoto M, Imai R. Antitumor activity of echinosporin. J Antibiot (Tokyo). 1985 Apr;38(4):490-5. PubMed PMID: 4008342.
6: Sato T, Kawamoto I, Oka T, Okachi R. A new antibiotic echinosporin (XK-213) - producing organism, isolation and characterization. J Antibiot (Tokyo). 1982 Mar;35(3):266-71. PubMed PMID: 7076574.
