Taccalonolide A - ≥99% , CAS No.108885-68-3

CAS: 108885-68-3 Cat. No.: T648501 Molecular Weight: 702.74 PubChem CID: 441685

GRADE & PURITY ≥99%

Synonyms

A904550 | CHEBI:9388 | AKOS037515195 | 16,24-Cycloergost-22-en-26-oicacid, 1,11,12,15-tetrakis(acetyloxy)-2,3-epoxy-7,23,25-trihydroxy-6-oxo-, g-lactone, (1a,2a,3a,5a,7b,11a,12a,15a,16b,24b,25S)- | Q27108373 | AC1L9BGV | DTXSID80910895 | PTTJLTMUKRRHAT-VJ

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

Taccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri , with cytotoxic and antimalarial activities Taccalonolide A causes G 2 -M accumulation, Bcl-2 phosphorylation and initiation of apoptosis Taccalonolide A is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug resistance protein 7 (MRP7), with an IC 50 of 622 nM for SK-OV-3 cells

Form:Solid

IC50& Target:microtubule

Specifications

Synonyms

A904550 | CHEBI:9388 | AKOS037515195 | 16, 24-Cycloergost-22-en-26-oicacid, 1, 11, 12, 15-tetrakis(acetyloxy)-2, 3-epoxy-7, 23, 25-trihydroxy-6-oxo-, g-lactone, (1a, 2a, 3a, 5a, 7b, 11a, 12a, 15a, 16b, 24b, 25S)- | Q27108373 | AC1L9BGV | DTXSID80910895 | PTTJLTMUKRRHAT-VJ

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Taccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri , with cytotoxic and antimalarial activities. Taccalonolide A causes G 2 -M accumulation, Bcl-2 phosphorylation and initiation of apoptosis. Tacca

Storage

Store at 2-8°C, Protected from light, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1C=C2C(C3C1C4(C(C3OC(=O)C)C5C(C(C4OC(=O)C)OC(=O)C)C6(C(CC7C(C6OC(=O)C)O7)C(=O)C5O)C)C)(C(C(=O)O2)(C)O)C
• IUPAC Name: [(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-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
• InChIKey: PTTJLTMUKRRHAT-VJAKQJMOSA-N
• INCHI: 1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)11-18-27(49-18)30(33)47-15(4)39/h10,12,17-18,20-24,26-31,42,44H,11H2,1-9H3/t12-,17-,18+,20+,21+,22-,23-,24+,26-,27+,28-,29+,30+,31+,33+,34-,35+,36-/m1/s1
• Isomeric SMILES: C[C@@H]1C=C2[C@@]([C@H]3[C@H]1[C@@]4([C@@H]([C@H]3OC(=O)C)[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
• Alternate CAS: 108885-68-3
• PubChem CID: 441685
• MeSH Entry Terms: taccalonolide A
• Molecular Weight: 702.74

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroid lactones

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroid lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Withanolides and derivatives
• Alternative Parents: Steroid esters 6-oxosteroids 7-hydroxysteroids Pentacarboxylic acids and derivatives Oxepanes Tetrahydrofurans Tertiary alcohols Enol esters Lactones Ketones Cyclic alcohols and derivatives Secondary alcohols Epoxides Dialkyl ethers Oxacyclic compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Withanolide-skeleton - Steroid ester - Hydroxysteroid - Oxosteroid - 6-oxosteroid - 7-hydroxysteroid - Pentacarboxylic acid or derivatives - Oxepane - Tetrahydrofuran - Tertiary alcohol - Cyclic alcohol - Enol ester - Secondary alcohol - Carboxylic acid ester - Lactone - Ketone - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Ether - Oxirane - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Alcohol - Organic oxide - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
• External Descriptors: Triterpenoids (C30)

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 702.700 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 8
• Exact Mass: 702.289 Da
• Monoisotopic Mass: 702.289 Da
• Topological Polar Surface Area: 202.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 1620.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 18
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1