MedKoo Cat#: 461402 | Name: Asimicin

Description:

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

Asimicin is a potent complex I inhibitor.

Chemical Structure

Asimicin
Asimicin
CAS#102989-24-2

Theoretical Analysis

MedKoo Cat#: 461402

Name: Asimicin

CAS#: 102989-24-2

Chemical Formula: C37H66O7

Exact Mass: 622.4809

Molecular Weight: 622.92

Elemental Analysis: C, 71.34; H, 10.68; O, 17.98

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Asimicin;
IUPAC/Chemical Name
(S)-3-((2R,13R)-2,13-dihydroxy-13-((2R,2'R,5R,5'R)-5'-((R)-1-hydroxyundecyl)octahydro-[2,2'-bifuran]-5-yl)tridecyl)-5-methylfuran-2(5H)-one
InChi Key
MBABCNBNDNGODA-UOCXRWNNSA-N
InChi Code
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31+,32+,33+,34+,35+,36+/m0/s1
SMILES Code
O=C1O[C@@H](C)C=C1C[C@H](O)CCCCCCCCCC[C@@H](O)[C@H]2CC[C@H]([C@@H]3O[C@@H]([C@H](O)CCCCCCCCCC)CC3)O2
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 622.92 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: Mangal M, Khan MI, Agarwal SM. Acetogenins as Potential Anticancer Agents. Anticancer Agents Med Chem. 2015;16(2):138-59. Review. PubMed PMID: 26118710. 2: Nakamaru-Ogiso E, Han H, Matsuno-Yagi A, Keinan E, Sinha SC, Yagi T, Ohnishi T. The ND2 subunit is labeled by a photoaffinity analogue of asimicin, a potent complex I inhibitor. FEBS Lett. 2010 Mar 5;584(5):883-8. doi: 10.1016/j.febslet.2010.01.004. Epub 2010 Jan 13. PubMed PMID: 20074573; PubMed Central PMCID: PMC2836797. 3: Zhao GX, Miesbauer LR, Smith DL, McLaughlin JL. Asimin, asiminacin, and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba. J Med Chem. 1994 Jun 24;37(13):1971-6. PubMed PMID: 8027979. 4: Avedissian H, Sinha SC, Yazbak A, Sinha A, Neogi P, Sinha SC, Keinan E. Total synthesis of asimicin and bullatacin. J Org Chem. 2000 Sep 22;65(19):6035-51. PubMed PMID: 10987938. 5: Shimada H, Grutzner JB, Kozlowski JF, McLaughlin JL. Membrane conformations and their relation to cytotoxicity of asimicin and its analogues. Biochemistry. 1998 Jan 20;37(3):854-66. PubMed PMID: 9454575. 6: Zhao GX, Chao JF, Zeng L, Rieser MJ, McLaughlin JL. The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba. Bioorg Med Chem. 1996 Jan;4(1):25-32. PubMed PMID: 8689234. 7: Ye Q, He K, Oberlies NH, Zeng L, Shi G, Evert D, McLaughlin JL. Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins. J Med Chem. 1996 Apr 26;39(9):1790-6. PubMed PMID: 8627602. 8: Marshall JA, Sabatini JJ. An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue. Org Lett. 2006 Aug 3;8(16):3557-60. PubMed PMID: 16869659. 9: Sinha SC, Chen Z, Huang ZZ, Nakamaru-Ogiso E, Pietraszkiewicz H, Edelstein M, Valeriote F. Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity. J Med Chem. 2008 Nov 27;51(22):7045-8. doi: 10.1021/jm801028c. PubMed PMID: 18975929; PubMed Central PMCID: PMC2670474. 10: Tinsley JM, Roush WR. Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. J Am Chem Soc. 2005 Aug 10;127(31):10818-9. PubMed PMID: 16076173. 11: Shi JF, Wu P, Jiang ZH, Wei XY. Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. Eur J Med Chem. 2014 Jan;71:219-28. doi: 10.1016/j.ejmech.2013.11.012. Epub 2013 Nov 15. PubMed PMID: 24308999. 12: Marshall JA, Piettre A, Paige MA, Valeriote F. A modular synthesis of annonaceous acetogenins. J Org Chem. 2003 Mar 7;68(5):1771-9. PubMed PMID: 12608790. 13: Rodrigues dos Santos Lima LA, Santos Pimenta LP, Diamantino Boaventura MA. Two new adjacent bis-tetrahydrofuran annonaceous acetogenins from seeds of Annona cornifolia. Planta Med. 2009 Jan;75(1):80-3. doi: 10.1055/s-0028-1088359. Epub 2008 Nov 27. PubMed PMID: 19039734. 14: Pomper KW, Lowe JD, Crabtree SB, Keller W. Identification of annonaceous acetogenins in the ripe fruit of the North American pawpaw ( Asimina triloba ). J Agric Food Chem. 2009 Sep 23;57(18):8339-43. doi: 10.1021/jf9018239. PubMed PMID: 19711911. 15: Nakamaru-Ogiso E, Kao MC, Chen H, Sinha SC, Yagi T, Ohnishi T. The membrane subunit NuoL(ND5) is involved in the indirect proton pumping mechanism of Escherichia coli complex I. J Biol Chem. 2010 Dec 10;285(50):39070-8. doi: 10.1074/jbc.M110.157826. Epub 2010 Sep 7. PubMed PMID: 20826797; PubMed Central PMCID: PMC2998099. 16: Masuya T, Murai M, Morisaka H, Miyoshi H. Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry. Biochemistry. 2014 Dec 16;53(49):7816-23. doi: 10.1021/bi501342w. Epub 2014 Dec 2. PubMed PMID: 25419630. 17: Alali FQ, Kaakeh W, Bennett GW, McLaughlin JL. Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae). J Econ Entomol. 1998 Jun;91(3):641-9. PubMed PMID: 9650513. 18: Ferreira JF, Peaden P, Keiser J. In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis: trematocidal plant alcoholic extracts. Parasitol Res. 2011 Dec;109(6):1585-92. doi: 10.1007/s00436-011-2418-0. Epub 2011 May 12. PubMed PMID: 21562762. 19: Chang FR, Liaw CC, Lin CY, Chou CJ, Chiu HF, Wu YC. New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata. Planta Med. 2003 Mar;69(3):241-6. PubMed PMID: 12677528. 20: Hui YH, Rupprecht JK, Liu YM, Anderson JE, Smith DL, Chang CJ, McLaughlin JL. Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. J Nat Prod. 1989 May-Jun;52(3):463-77. PubMed PMID: 2778448.