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Taccalonolide B

CAT: 0804-HY-N3028-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N3028-01Size:1 mg
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Description
Taccalonolide B is microtubule stabilizer isolated from Tacca plantaginea, with antitumor activity. Taccalonolide B is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug-resistance protein (MRP7) . Taccalonolide B inhibits growth of SK-OV-3 cells with an IC50 of 208 nM[1][2].
CAS Number
108885-69-4
UNSPSC
12352005
Target
Microtubule/Tubulin
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Cytoskeleton
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/taccalonolide-b.html
Purity
99.46
Solubility
DMSO : ≥ 50 mg/mL
Smiles
C[C@]1([C@]2([H])C[C@H](O3)[C@H]3[C@@H]1OC(C)=O)[C@]4([H])[C@]([C@@H](O)C2=O)([H])[C@@]5([H])[C@@](C)([C@]6([H])[C@@]([C@](C(OC7=O)=C[C@H]6C)([C@@]7(O)C)C)([H])[C@@H]5O)[C@@H](OC(C)=O)[C@H]4OC(C)=O
Molecular Formula
C34H44O13
Molecular Weight
660.71
References & Citations
[1]LiangChen Zhong, et al. Steroidal bitter principles from tacca plantaginea structures of taccalonolide A and B. Tetrahedron Letters. 1987, 28 (15) : 1673-1675.|[2]Risinger AL, et al. The taccalonolides: microtubule stabilizers that circumvent clinically relevant taxane resistance mechanisms. Cancer Res. 2008 Nov 1;68 (21) :8881-8.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Taccalonolide B

Taccalonolide B has been reported in Tacca chantrieri and Tacca plantaginea with data available.

CAS Number108885-69-4
PubChem CID56662029
IUPAC Name[(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14-diacetyloxy-3,22,25-trihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-13-yl] acetate
Molecular FormulaC34H44O13
Molecular Weight660.7
XLogP1.1
Topological Polar Surface Area195
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count13
Rotatable Bond Count6
Heavy Atom Count47
Formal Charge0
Complexity1510
SMILES
C[C@@H]1C=C2[C@@]([C@H]3[C@H]1[C@@]4([C@@H]([C@H]3O)[C@H]5[C@H]([C@@H]([C@@H]4OC(=O)C)OC(=O)C)[C@@]6([C@H](C[C@H]7[C@@H]([C@@H]6OC(=O)C)O7)C(=O)[C@@H]5O)C)C)([C@](C(=O)O2)(C)O)C
InChI
InChI=1S/C34H44O13/c1-11-9-17-33(7,34(8,42)30(41)47-17)22-19(11)32(6)20(25(22)40)18-21(27(43-12(2)35)29(32)45-14(4)37)31(5)15(23(38)24(18)39)10-16-26(46-16)28(31)44-13(3)36/h9,11,15-16,18-22,24-29,39-40,42H,10H2,1-8H3/t11-,15-,16+,18+,19+,20-,21-,22+,24-,25-,26+,27+,28+,29+,31+,32-,33+,34-/m1/s1
InChIKey
FFQOXBQSZPYHSA-MPOUNFKCSA-N
Chemical Structure
2D Structure
2D structure of Taccalonolide B
CAS: 108885-69-4
CID: 56662029
Formula: C34H44O13
MW: 660.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight660.7
XLogP31.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count13
Rotatable Bond Count6
Exact Mass660.27819145
Monoisotopic Mass660.27819145
Topological Polar Surface Area195 Ų
Heavy Atom Count47
Formal Charge0
Complexity1510
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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