Physicochemical Properties
| Molecular Formula | C28H41NO9 |
| Molecular Weight | 535.6264 |
| Exact Mass | 535.28 |
| Elemental Analysis | C, 62.79; H, 7.72; N, 2.62; O, 26.88 |
| CAS # | 1426953-21-0 |
| PubChem CID | 71665768 |
| Appearance | White to off-white solid powder |
| LogP | 1.9 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 38 |
| Complexity | 960 |
| Defined Atom Stereocenter Count | 9 |
| SMILES | C[C@H]1C[C@H]([C@H](O[C@H]1C/C=C(\C)/C=C/[C@@H]2[C@H]([C@@]3(C[C@H](O2)CC(=O)O)CO3)O)C)NC(=O)/C=C\[C@H](C)OC(=O)C |
| InChi Key | GJKQDOMCDFJANR-FUDLAKRJSA-N |
| InChi Code | InChI=1S/C28H41NO9/c1-16(7-10-24-27(34)28(15-35-28)14-21(38-24)13-26(32)33)6-9-23-17(2)12-22(19(4)37-23)29-25(31)11-8-18(3)36-20(5)30/h6-8,10-11,17-19,21-24,27,34H,9,12-15H2,1-5H3,(H,29,31)(H,32,33)/b10-7+,11-8-,16-6+/t17-,18-,19+,21+,22+,23-,24+,27+,28+/m0/s1 |
| Chemical Name | 2-[(3R,4R,5R,7S)-5-[(1E,3E)-5-[(2S,3S,5R,6R)-5-[[(Z,4S)-4-acetyloxypent-2-enoyl]amino]-3,6-dimethyloxan-2-yl]-3-methylpenta-1,3-dienyl]-4-hydroxy-1,6-dioxaspiro[2.5]octan-7-yl]acetic acid |
| Synonyms | Thailanstatin A, TST-A; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | The natural product Thailanstatin A (TST-A) is a strong antiproliferative that is derived from Burkholderia thailandensis MSMB43[2]. With GI50s in the single nM range (1.11-2.69 nM), thailanstatin A (DU-145, NCI-H232A, MDA-MB-231, and SKOV-3 cells) demonstrates strong antiproliferative activities[3]. |
| References |
[1]. Natural Product Splicing Inhibitors: A New Class of Antibody-Drug Conjugate (ADC) Payloads. Bioconjug Chem. 2016;27(8):1880-1888. [2]. Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition. J Org Chem. 2018;83(9):5187-5198. [3]. Genomics-guided discovery of thailanstatins A, B, and C As pre-mRNA splicing inhibitors and antiproliferative agents from Burkholderia thailandensis MSMB43. J Nat Prod. 2013;76(4):685-693. |
| Additional Infomation |
Thailanstatin A is a C-glycosyl compound. Thailanstatin A has been reported in Burkholderia thailandensis with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~466.74 mM） |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.88 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8670 mL | 9.3348 mL | 18.6696 mL | |
| 5 mM | 0.3734 mL | 1.8670 mL | 3.7339 mL | |
| 10 mM | 0.1867 mL | 0.9335 mL | 1.8670 mL |