Swinholide A

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

MedKoo CAT#: 463495

CAS#: 95927-67-6

Description: Swinholide A is a natural microfilament, disrupting marine toxin that stabilizes actin dimers and severs actin filaments.

Chemical Structure

Swinholide A
CAS# 95927-67-6

Theoretical Analysis

MedKoo Cat#: 463495
Name: Swinholide A
CAS#: 95927-67-6
Chemical Formula: C78H132O20
Exact Mass: 1388.9312
Molecular Weight: 1389.894
Elemental Analysis: C, 67.40; H, 9.57; O, 23.02

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.

Request quote for custom synthesis

Synonym: Swinholide A; Swinholide-A;

IUPAC/Chemical Name: (1R,3S,5E,7E,11S,12S,13R,15S,16S,17S,19S,23R,25R,27Z,29E,33S,34S,35R,37S,38S,39S,41S)-3,13,15,25,35,37-hexahydroxy-11-((2S,3S,4R)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)-4-methylhexan-2-yl)-33-((2S,3S,4S)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)-4-methylhexan-2-yl)-17,39-dimethoxy-6,12,16,28,34,38-hexamethyl-10,32,45,46-tetraoxatricyclo[,23]hexatetraconta-5,7,21,27,29,43-hexaene-9,31-dione


InChi Code: InChI=1S/C78H132O20/c1-45-23-29-57(79)37-59-19-17-21-61(95-59)41-71(91-15)52(8)68(82)44-70(84)54(10)78(56(12)76(88)48(4)28-32-64-40-66(90-14)36-50(6)94-64)98-74(86)34-26-46(2)24-30-58(80)38-60-20-18-22-62(96-60)42-72(92-16)51(7)67(81)43-69(83)53(9)77(97-73(85)33-25-45)55(11)75(87)47(3)27-31-63-39-65(89-13)35-49(5)93-63/h17-20,23-26,33-34,47-72,75-84,87-88H,21-22,27-32,35-44H2,1-16H3/b33-25+,34-26+,45-23-,46-24+/t47-,48+,49-,50-,51-,52-,53-,54-,55-,56-,57+,58-,59-,60-,61-,62-,63-,64-,65+,66+,67-,68-,69+,70+,71-,72-,75-,76-,77-,78-/m0/s1

SMILES Code: O=C(O[C@H]([C@H]([C@@H](O)[C@H](C)CC[C@@H]1O[C@@H](C)C[C@@H](OC)C1)C)[C@@H](C)[C@H](O)C[C@H](O)[C@H](C)[C@@H](OC)C[C@]2([H])CC=C[C@@](O2)([H])C[C@H](O)C/C=C(C)\C=C\3)/C=C/C(C)=C/C[C@H](O)C[C@](O4)([H])C=CC[C@@]4([H])C[C@H](OC)[C@@H](C)[C@@H](O)C[C@@H](O)[C@H](C)[C@@H]([C@H]([C@@H](O)[C@@H](C)CC[C@@H]5O[C@@H](C)C[C@@H](OC)C5)C)OC3=O

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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1389.894 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.


Dilution Calculator

Calculate the dilution required to prepare a stock solution.

1: Reher R, Kim HW, Zhang C, Mao HH, Wang M, Nothias LF, Caraballo-Rodriguez AM, Glukhov E, Teke B, Leao T, Alexander KL, Duggan BM, Van Everbroeck EL, Dorrestein PC, Cottrell GW, Gerwick WH. A Convolutional Neural Network-Based Approach for the Rapid Annotation of Molecularly Diverse Natural Products. J Am Chem Soc. 2020 Mar 4;142(9):4114-4120. doi: 10.1021/jacs.9b13786. Epub 2020 Feb 21. PMID: 32045230; PMCID: PMC7210566.

2: Ohyoshi T , Takano A , Namiki M , Ogura T , Miyazaki Y , Ebihara Y , Takeno K , Hayakawa I , Kigoshi H . Development of a novel inducer of protein-protein interactions based on aplyronine A. Chem Commun (Camb). 2018 Aug 21;54(68):9537-9540. doi: 10.1039/c8cc04613a. PMID: 30094443.

3: Lim TC, Hatano T, Kamnev A, Balasubramanian MK, Chew TG. Equatorial Assembly of the Cell-Division Actomyosin Ring in the Absence of Cytokinetic Spatial Cues. Curr Biol. 2018 Mar 19;28(6):955-962.e3. doi: 10.1016/j.cub.2018.01.088. Epub 2018 Mar 1. PMID: 29502950; PMCID: PMC5863765.

4: Humisto A, Jokela J, Liu L, Wahlsten M, Wang H, Permi P, Machado JP, Antunes A, Fewer DP, Sivonen K. The Swinholide Biosynthesis Gene Cluster from a Terrestrial Cyanobacterium, Nostoc sp. Strain UHCC 0450. Appl Environ Microbiol. 2018 Jan 17;84(3):e02321-17. doi: 10.1128/AEM.02321-17. PMID: 29150506; PMCID: PMC5772238.

5: Issac M, Aknin M, Gauvin-Bialecki A, De Voogd N, Ledoux A, Frederich M, Kashman Y, Carmeli S. Cyclotheonellazoles A-C, Potent Protease Inhibitors from the Marine Sponge Theonella aff. swinhoei. J Nat Prod. 2017 Apr 28;80(4):1110-1116. doi: 10.1021/acs.jnatprod.7b00028. Epub 2017 Feb 16. PMID: 28207261.

6: Shin I, Hong S, Krische MJ. Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation. J Am Chem Soc. 2016 Nov 2;138(43):14246-14249. doi: 10.1021/jacs.6b10645. Epub 2016 Oct 25. PMID: 27779393; PMCID: PMC5096380.

7: Holzinger A, Blaas K. Actin-Dynamics in Plant Cells: The Function of Actin- Perturbing Substances: Jasplakinolide, Chondramides, Phalloidin, Cytochalasins, and Latrunculins. Methods Mol Biol. 2016;1365:243-61. doi: 10.1007/978-1-4939-3124-8_13. PMID: 26498789; PMCID: PMC4869834.

8: Shin I, Krische MJ. Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols. Org Lett. 2015 Oct 2;17(19):4686-9. doi: 10.1021/acs.orglett.5b02056. PMID: 26375150; PMCID: PMC4686429.

9: Bergman O, Mayzel B, Anderson MA, Shpigel M, Hill RT, Ilan M. Examination of marine-based cultivation of three demosponges for acquiring bioactive marine natural products. Mar Drugs. 2011;9(11):2201-19. doi: 10.3390/md9112201. Epub 2011 Nov 7. PMID: 22163182; PMCID: PMC3229231.

10: De Marino S, Festa C, D'Auria MV, Cresteil T, Debitus C, Zampella A. Swinholide J, a potent cytotoxin from the marine sponge Theonella swinhoei. Mar Drugs. 2011;9(6):1133-41. doi: 10.3390/md9061133. Epub 2011 Jun 22. PMID: 21747751; PMCID: PMC3131564.

11: Huynh C, Ren G, Papillon J, Guillemette J, Takano T, Cybulsky AV. The cytoprotective role of Ras in complement-mediated glomerular epithelial cell injury. Clin Immunol. 2009 May;131(2):343-53. doi: 10.1016/j.clim.2008.11.012. Epub 2009 Jan 9. PMID: 19138568.

12: Zhang J, Guo H, Mi Z, Gao C, Bhattacharya S, Li J, Kuo PC. EF1A1-actin interactions alter mRNA stability to determine differential osteopontin expression in HepG2 and Hep3B cells. Exp Cell Res. 2009 Jan 15;315(2):304-12. doi: 10.1016/j.yexcr.2008.10.042. Epub 2008 Nov 7. PMID: 19026636.

13: Kartika R, Frein JD, Taylor RE. Electrophile-induced ether transfer: stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans. J Org Chem. 2008 Jul 18;73(14):5592-4. doi: 10.1021/jo800704d. Epub 2008 Jun 21. PMID: 18570473.

14: Stanley FM. Insulin-increased prolactin gene expression requires actin treadmilling: potential role for p21 activated kinase. Endocrinology. 2007 Dec;148(12):5874-83. doi: 10.1210/en.2007-0127. Epub 2007 Sep 20. PMID: 17884942.

15: Nunes P, Haines N, Kuppuswamy V, Fleet DJ, Stewart BA. Synaptic vesicle mobility and presynaptic F-actin are disrupted in a N-ethylmaleimide-sensitive factor allele of Drosophila. Mol Biol Cell. 2006 Nov;17(11):4709-19. doi: 10.1091/mbc.e06-03-0253. Epub 2006 Aug 16. PMID: 16914524; PMCID: PMC1635382.

16: Bourne J, Morgan JR, Pieribone VA. Actin polymerization regulates clathrin coat maturation during early stages of synaptic vesicle recycling at lamprey synapses. J Comp Neurol. 2006 Aug 1;497(4):600-9. doi: 10.1002/cne.21006. PMID: 16739194.

17: Saito M, Matsuura T, Masaki T, Maehashi H, Shimizu K, Hataba Y, Iwahori T, Suzuki T, Braet F. Reconstruction of liver organoid using a bioreactor. World J Gastroenterol. 2006 Mar 28;12(12):1881-8. doi: 10.3748/wjg.v12.i12.1881. PMID: 16609994; PMCID: PMC4087513.

18: Genescà M, Sola A, Hotter G. Actin cytoskeleton derangement induces apoptosis in renal ischemia/reperfusion. Apoptosis. 2006 Apr;11(4):563-71. doi: 10.1007/s10495-006-4937-1. PMID: 16528472.

19: Piel J. Bacterial symbionts: prospects for the sustainable production of invertebrate-derived pharmaceuticals. Curr Med Chem. 2006;13(1):39-50. PMID: 16457638.

20: Youssef DT, Mooberry SL. Hurghadolide A and swinholide I, potent actin- microfilament disrupters from the Red Sea sponge Theonella swinhoei. J Nat Prod. 2006 Jan;69(1):154-7. doi: 10.1021/np050404a. PMID: 16441091.