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MedKoo Cat#: 598352 | Name: Holotoxin A1

Description:

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

Holotoxin A1 is a bioactive chemical.

Chemical Structure

Holotoxin A1
Holotoxin A1
CAS#85344-35-0

Theoretical Analysis

MedKoo Cat#: 598352

Name: Holotoxin A1

CAS#: 85344-35-0

Chemical Formula: C66H104O31

Exact Mass: 1392.6562

Molecular Weight: 1393.52

Elemental Analysis: C, 56.89; H, 7.52; O, 35.59

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Holotoxin A1;
IUPAC/Chemical Name
(3S,3aS,5aS,5bR,7aR,9R,11aS,13aR)-9-(((2S,3S,4S,5R)-5-(((2S,3S,4R,5R,6R)-4-(((2S,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-(((2R,3R,4S,5S,6S)-5-(((2R,3R,4R,5R)-4-(((2R,3R,4R,5R,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxytetrahydro-2H-pyran-3-yl)oxy)-3,5a,8,8,11a-pentamethyl-3-(4-methylpent-4-en-1-yl)-3,3a,5,5a,5b,6,7,7a,8,9,10,11,11a,13-tetradecahydro-1H,4H-naphtho[2',1':4,5]indeno[1,7a-c]furan-1,4-dione
InChi Key
ZFOUAAXBXISYFU-WAIQHJBGSA-N
InChi Code
InChI=1S/C66H104O31/c1-26(2)12-11-17-65(8)54-30(70)20-64(7)29-13-14-36-62(4,5)37(16-18-63(36,6)28(29)15-19-66(54,64)61(82)97-65)92-53-41(75)35(91-57-47(81)52(40(74)34(23-69)88-57)95-59-46(80)51(84-10)39(73)33(22-68)90-59)25-86-60(53)96-56-43(77)42(76)48(27(3)87-56)93-55-44(78)49(31(71)24-85-55)94-58-45(79)50(83-9)38(72)32(21-67)89-58/h15,27,29,31-60,67-69,71-81H,1,11-14,16-25H2,2-10H3/t27-,29-,31+,32-,33+,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44+,45+,46-,47-,48+,49+,50+,51+,52+,53-,54+,55+,56+,57-,58+,59-,60-,63+,64-,65-,66-/m0/s1
SMILES Code
C[C@@]1(CC[C@H](C(C)(C)[C@@H]1CC[C@@H]2[C@]3(C)CC([C@@H]4[C@@](CCCC(C)=C)(C)O5)=O)O[C@@H]6[C@H](O[C@@H]7[C@H](O)[C@H](O)[C@H](O[C@@H]8[C@H](O)[C@H](O[C@@H]9[C@H](O)[C@H](OC)[C@H](O)[C@H](CO)O9)[C@H](O)CO8)[C@H](C)O7)OC[C@H]([C@@H]6O)O[C@@H]%10O[C@H](CO)[C@H]([C@H]([C@@H]%10O)O[C@@H]%11O[C@H](CO)[C@H]([C@H]([C@@H]%11O)OC)O)O)C2=CC[C@]34C5=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,393.52 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
1: Taylor M, Banerjee T, Ray S, Tatulian SA, Teter K. Protein-disulfide isomerase displaces the cholera toxin A1 subunit from the holotoxin without unfolding the A1 subunit. J Biol Chem. 2011 Jun 24;286(25):22090-100. doi: 10.1074/jbc.M111.237966. Epub 2011 May 4. PubMed PMID: 21543321; PubMed Central PMCID: PMC3121353. 2: Bradshaw M, Tepp WH, Whitemarsh RC, Pellett S, Johnson EA. Holotoxin Activity of Botulinum Neurotoxin Subtype A4 Originating from a Nontoxigenic Clostridium botulinum Expression System. Appl Environ Microbiol. 2014 Dec;80(23):7415-22. doi: 10.1128/AEM.01795-14. Epub 2014 Sep 19. PubMed PMID: 25239905; PubMed Central PMCID: PMC4249187. 3: Aminin DL, Lebedev AV, Levitskiĭ DO. [The effect of holotoxin A1 on transport of calcium ions across the lipid models of biological membranes]. Biokhimiia. 1990 Feb;55(2):270-5. Russian. PubMed PMID: 2160291. 4: Sabo T, Kronman C, Mazor O. Ricin-Holotoxin-Based Vaccines: Induction of Potent Ricin-Neutralizing Antibodies. Methods Mol Biol. 2016;1403:683-94. doi: 10.1007/978-1-4939-3387-7_38. PubMed PMID: 27076160. 5: Ivanov AS, Khalilov EM, Solov'eva EF, Stonik VA, Mal'tsev II. [Analysis of free cholesterol levels in human serum using holotoxin A1]. Vopr Med Khim. 1986 Sep-Oct;32(5):132-4. Russian. PubMed PMID: 3776109. 6: Aminin DL, Osipov AN, Korepanova EA, Anisimov MM. [Effect of holotoxin A1 on microviscosity of model and biological membranes]. Biofizika. 1989 Mar-Apr;34(2):318-9. Russian. PubMed PMID: 2742908. 7: Cohen O, Mechaly A, Sabo T, Alcalay R, Aloni-Grinstein R, Seliger N, Kronman C, Mazor O. Characterization and epitope mapping of the polyclonal antibody repertoire elicited by ricin holotoxin-based vaccination. Clin Vaccine Immunol. 2014 Nov;21(11):1534-40. doi: 10.1128/CVI.00510-14. Epub 2014 Sep 10. PubMed PMID: 25209559; PubMed Central PMCID: PMC4248767. 8: Wang HH, Riding S, Lindo P, Singh BR. Endopeptidase activities of botulinum neurotoxin type B complex, holotoxin, and light chain. Appl Environ Microbiol. 2010 Oct;76(19):6658-63. doi: 10.1128/AEM.00731-10. Epub 2010 Aug 6. PubMed PMID: 20693440; PubMed Central PMCID: PMC2950459. 9: Li S, Wang Y, Jiang T, Wang H, Yang S, Lv Z. Absorption and Transport of Sea Cucumber Saponins from Apostichopus japonicus. Mar Drugs. 2016 Jun 17;14(6). pii: E114. doi: 10.3390/md14060114. PubMed PMID: 27322290; PubMed Central PMCID: PMC4926073. 10: Tinker JK, Erbe JL, Hol WG, Holmes RK. Cholera holotoxin assembly requires a hydrophobic domain at the A-B5 interface: mutational analysis and development of an in vitro assembly system. Infect Immun. 2003 Jul;71(7):4093-101. PubMed PMID: 12819100; PubMed Central PMCID: PMC162025. 11: Yun SH, Park ES, Shin SW, Ju MH, Han JY, Jeong JS, Kim SH, Stonik VA, Kwak JY, Park JI. By activating Fas/ceramide synthase 6/p38 kinase in lipid rafts, stichoposide D inhibits growth of leukemia xenografts. Oncotarget. 2015 Sep 29;6(29):27596-612. doi: 10.18632/oncotarget.4820. PubMed PMID: 26318294; PubMed Central PMCID: PMC4695011. 12: Tamura S, Asanuma H, Tomita T, Komase K, Kawahara K, Danbara H, Hattori N, Watanabe K, Suzuki Y, Nagamine T, et al. Escherichia coli heat-labile enterotoxin B subunits supplemented with a trace amount of the holotoxin as an adjuvant for nasal influenza vaccine. Vaccine. 1994 Sep;12(12):1083-9. PubMed PMID: 7998417. 13: Hagiwara Y, Iwasaki T, Asanuma H, Sato Y, Sata T, Aizawa C, Kurata T, Tamura S. Effects of intranasal administration of cholera toxin (or Escherichia coli heat-labile enterotoxin) B subunits supplemented with a trace amount of the holotoxin on the brain. Vaccine. 2001 Feb 8;19(13-14):1652-60. PubMed PMID: 11166888. 14: Ueno Y, Ohara M, Kawamoto T, Fujiwara T, Komatsuzawa H, Oswald E, Sugai M. Biogenesis of the Actinobacillus actinomycetemcomitans cytolethal distending toxin holotoxin. Infect Immun. 2006 Jun;74(6):3480-7. PubMed PMID: 16714579; PubMed Central PMCID: PMC1479298. 15: Treiber N, Reinert DJ, Carpusca I, Aktories K, Schulz GE. Structure and mode of action of a mosquitocidal holotoxin. J Mol Biol. 2008 Aug 1;381(1):150-9. doi: 10.1016/j.jmb.2008.05.067. Epub 2008 Jun 3. PubMed PMID: 18586267. 16: Noy-Porat T, Rosenfeld R, Ariel N, Epstein E, Alcalay R, Zvi A, Kronman C, Ordentlich A, Mazor O. Isolation of Anti-Ricin Protective Antibodies Exhibiting High Affinity from Immunized Non-Human Primates. Toxins (Basel). 2016 Mar 3;8(3). pii: E64. doi: 10.3390/toxins8030064. PubMed PMID: 26950154; PubMed Central PMCID: PMC4810209. 17: Mats MN, Korkhov VV, Stepanov VR, Kupera EV, Oleĭnikova GK, Anisimov MM. [The contraceptive activity of triterpene glycosides--the total sum of holotoxins A1 and B1 and holothurin A in an experiment]. Farmakol Toksikol. 1990 Mar-Apr;53(2):45-7. Russian. PubMed PMID: 2369955. 18: Aminin DL, Anisimov MM. [Holotoxin content in the tissues of the holothurian Stichopus japonicus at different seasons of the year and their effect on oocyte maturation]. Zh Evol Biokhim Fiziol. 1987 Jul-Aug;23(4):545-7. Russian. PubMed PMID: 3673372. 19: Raghavan M, Gotto JW, Scott JV, Schutt CE. Preliminary X-ray crystallographic analysis of holotoxin from Bordetella pertussis. J Mol Biol. 1990 Jun 5;213(3):411-4. PubMed PMID: 2352276. 20: Mazeĭka AN, Kostetskiĭ EIa, Sanina NM, Popov AM, Kalinin VI, Li IA. [Elaboration of immune stimulating lipid-saponin subunit antigen carrier based on glycolipid monogalactosyldiacylglycerol from sea macrophytes and triterpene glycosides from Cucumaria japonica]. Biofizika. 2013 Sep-Oct;58(5):786-95. Russian. PubMed PMID: 25481946.