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Thailanstatin A

CAT: 0804-HY-129589-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-129589-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Thailanstatin A is an ultra-potent inhibitor of eukaryotic RNA splicing (IC50=650 nM) . Thailanstatin A exerts effects via non-covalent binding to the SF3b subunit of the U2 snRNA subcomplex of the spliceosome and shows low-nM to sub-nM IC50s against multiple cancer cell lines. Thailanstatin A, a payload for ADCs, is conjugated to the lysines on trastuzumab yielding “linker-less” ADC[1][2][3].
CAS Number
1426953-21-0
UNSPSC
12352203
Target
ADC Payload
Type
ADC Related
Related Pathways
Antibody-drug Conjugate/ADC Related
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/thailanstatin-a.html
Purity
99.71
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(O)C[C@@H](O[C@H](/C=C/C(C)=C/C[C@H]1[C@@H](C)C[C@@H](NC(/C=C\[C@@H](OC(C)=O)C)=O)[C@@H](C)O1)[C@H]2O)C[C@]32CO3
Molecular Formula
C28H41NO9
Molecular Weight
535.63
References & Citations
[1]Puthenveetil S, et al. Natural Product Splicing Inhibitors: A New Class of Antibody-Drug Conjugate (ADC) Payloads. Bioconjug Chem. 2016;27 (8) :1880-1888.|[2]Ghosh AK, et al. Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition. J Org Chem. 2018;83 (9) :5187-5198.|[3]Liu X, et al. 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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
ADC Related
Clinical Information
No Development Reported

Chemical Information

Thailanstatin A

Thailanstatin A is a C-glycosyl compound.

CAS Number1426953-21-0
PubChem CID71665768
IUPAC Name2-[(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
Molecular FormulaC28H41NO9
Molecular Weight535.6
XLogP1.9
Topological Polar Surface Area144
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count11
Heavy Atom Count38
Formal Charge0
Complexity960
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
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
InChIKey
GJKQDOMCDFJANR-FUDLAKRJSA-N
Chemical Structure
2D Structure
2D structure of Thailanstatin A
CAS: 1426953-21-0
CID: 71665768
Formula: C28H41NO9
MW: 535.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight535.6
XLogP31.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count11
Exact Mass535.27813189
Monoisotopic Mass535.27813189
Topological Polar Surface Area144 Ų
Heavy Atom Count38
Formal Charge0
Complexity960
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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MBS5820746MC-VC-PAB-Cyclohexanediamine-Thailanstatin A

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