Basic information
- CAS
108885-68-3- Standard SMILES
CC(=O)O[C@@H]1[C@H]2[C@H]3[C@H]([C@H](OC(C)=O)[C@H](OC(C)=O)[C@]2(C)[C@@H]2[C@@H]1[C@]1(C)C(=C[C@H]2C)OC(=O)[C@@]1(C)O)[C@]1(C)[C@H](C[C@@H]2O[C@@H]2[C@@H]1OC(C)=O)C(=O)[C@@H]3O- InChIKey
PTTJLTMUKRRHAT-VJAKQJMOSA-N- Molecular formula
- C36H46O14
- Average molar mass
- 702.7 g/mol
- Monoisotopic mass
- 702.28875614
Overview
Taccalonolide A is a withanolide.
Names & identifiers
- Preferred name
- Taccalonolide A
- IUPAC
- [(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
- English name
- Taccalonolide A
- Molecular formula
- C36H46O14
- Molecular weight
- 702.74
Names & synonyms
Taccalonolide A108885-68-3[(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(2R,3R,5S)-2-(1-hydroxy-1-methyl-ethyl)-5-[(3R,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]tetrahydropyran-3-ol((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(2R,3R,5S)-2-(1-hydroxy-1-methyl-ethyl)-5-((3R,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-17-yl)tetrahydropyran-3-olRefChem:187100CHEMBL1821838Potato ketolide AC08635AC1L9BGVCHEBI:9388
Show more names
Rhizolactone A.
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 202 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 8
- Heavy atoms
- 50
- Formal charge
- 0
- Complexity
- 1,620
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Withanolides and derivatives [ST0116]
Physicochemical properties
- Boiling point
- 776.8 · 776.8±60.0 °C(Predicted)
- Density
- 1.41 · 1.41±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- pka
- 11.56 · 11.56±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- PTTJLTMUKRRHAT-VJAKQJMOSA-N
Chemistry & industry
Applications
UsesTaccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri, with cytotoxic and antimalarial activities[1][2]. Taccalonolide A causes G2-M accumulation, Bcl-2 phosphorylation and initiation of apoptosis[1]. Taccalonolide A is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug resistance protein 7 (MRP7), with an IC50 of 622 nM for SK-OV-3 cells[3].
Suppliers71 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd+86-13119157289 · [email protected]
Related reactions
2 records
Compound notes
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