Verticilide

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

MedKoo CAT#: 565763

CAS#: N/A

Description: Verticilide is a natural insect ryanodine receptor (ryr) antagonist


Price and Availability

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Verticilide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565763
Name: Verticilide
CAS#: N/A
Chemical Formula: C44H76N4O12
Exact Mass: 852.546
Molecular Weight: 853.108
Elemental Analysis: C, 61.95; H, 8.98; N, 6.57; O, 22.50


Synonym: Verticilide

IUPAC/Chemical Name: (3S,6R,9S,12R,15S,18R,21S,24R)-3,4,9,10,15,16,21,22-Octamethyl-6,12,18,24-tetrapentyl-1,7,13,19-tetraoxa-4,10,16,22-tetrazacyclotetracosane-2,5,8,11,14,17,20,23-octone

InChi Key: CMEGQABRBDDBTQ-NQRIZWSQSA-N

InChi Code: InChI=1S/C44H76N4O12/c1-13-17-21-25-33-37(49)45(9)30(6)42(54)58-35(27-23-19-15-3)39(51)47(11)32(8)44(56)60-36(28-24-20-16-4)40(52)48(12)31(7)43(55)59-34(26-22-18-14-2)38(50)46(10)29(5)41(53)57-33/h29-36H,13-28H2,1-12H3/t29-,30-,31-,32-,33+,34+,35+,36+/m0/s1

SMILES Code: O=C([C@H](C)N(C)C([C@@H](CCCCC)OC([C@H](C)N(C)C([C@@H](CCCCC)OC([C@H](C)N(C)C([C@@H](CCCCC)OC([C@H](C)N1C)=O)=O)=O)=O)=O)=O)O[C@H](CCCCC)C1=O


Technical Data

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:
>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).

Harmonized System Code:
2934.99.90.01


References

1: Batiste SM, Blackwell DJ, Kim K, Kryshtal DO, Gomez-Hurtado N, Rebbeck RT, Cornea RL, Johnston JN, Knollmann BC. Unnatural verticilide enantiomer inhibits type 2 ryanodine receptor-mediated calcium leak and is antiarrhythmic. Proc Natl Acad Sci U S A. 2019 Mar 12;116(11):4810-4815. doi: 10.1073/pnas.1816685116. Epub 2019 Feb 21. PubMed PMID: 30792355; PubMed Central PMCID: PMC6421472.

2: Monma S, Sunazuka T, Nagai K, Arai T, Shiomi K, Matsui R, Omura S. Verticilide: elucidation of absolute configuration and total synthesis. Org Lett. 2006 Nov 23;8(24):5601-4. PubMed PMID: 17107082.

3: Shiomi K, Matsui R, Kakei A, Yamaguchi Y, Masuma R, Hatano H, Arai N, Isozaki M, Tanaka H, Kobayashi S, Turberg A, Omura S. Verticilide, a new ryanodine-binding inhibitor, produced by Verticillium sp. FKI-1033. J Antibiot (Tokyo). 2010 Feb;63(2):77-82. doi: 10.1038/ja.2009.126. Epub 2010 Jan 8. PubMed PMID: 20057513.

4: Ohshiro T, Matsuda D, Kazuhiro T, Uchida R, Nonaka K, Masuma R, Tomoda H. New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679. J Antibiot (Tokyo). 2012 May;65(5):255-62. doi: 10.1038/ja.2012.12. Epub 2012 Mar 14. PubMed PMID: 22415459.

5: D'Amato A, Della Sala G, Izzo I, Costabile C, Masuda Y, De Riccardis F. Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides. Molecules. 2018 Jul 19;23(7). pii: E1779. doi: 10.3390/molecules23071779. PubMed PMID: 30029532; PubMed Central PMCID: PMC6100324.