Atractyloside A
Basic information
- CAS
126054-77-1- Standard SMILES
CC(C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H]1CC[C@](O)(CO)[C@H]2CC(=O)[C@@](C)(O)[C@@H]2C1- InChIKey
QNBLVYVBWDIWDM-BSLJOXIBSA-N- Molecular formula
- C21H36O10
- Average molar mass
- 448.5 g/mol
- Monoisotopic mass
- 448.23084734
Overview
Atractyloside A is a terpene glycoside.
Names & identifiers
- Preferred name
- Atractyloside A
- IUPAC
- (3S,3aR,5R,8R,8aS)-3,8-dihydroxy-8-(hydroxymethyl)-3-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-3a,4,5,6,7,8a-hexahydro-1H-azulen-2-one
- English name
- (1S,3aβ,8aα)-1-Methyl-1α,4α-dihydroxy-4-(hydroxymethyl)-7β-[1-methyl-1-(β-D-glucopyranosyloxy)ethyl]decahydroazulene-2-one
- Molecular formula
- C21H36O10
- Molecular weight
- 448.51
Names & synonyms
Atractyloside A126054-77-1(3S,3aR,5R,8R,8aS)-3,8-dihydroxy-8-(hydroxymethyl)-3-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-3a,4,5,6,7,8a-hexahydro-1H-azulen-2-one(3S,3aR,5R,8R,8aS)-3,8-dihydroxy-8-(hydroxymethyl)-3-methyl-5-(2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxypropan-2-yl)-3a,4,5,6,7,8a-hexahydro-1H-azulen-2-oneRefChem:115472AtractylosideACHEBI:138832AKOS030526368(1S,3aS,4R,7R,8aR)-1,4-Dihydroxy-4-(hydroxymethyl)-1-methyl-7-(2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propan-2-yl)octahydroazulen-2(1H)-oneAC-34082BS-148652(1H)-Azulenone,7-[1-(b-D-glucopyranosyloxy)-1-methylethyl]octahydro-1,4-dihydroxy-4-(hydroxymethyl)-1-methyl-, (1S,3aS,4R,7R,8aR)-
Show more names
Atractyloside A, >98%Atractyloside A 126054-77-1Atractyloside A, 10 mM in DMSO(3S,3aR,5R,8R,8aS)-3,8-dihydroxy-8-(hydroxymethyl)-3-methyl-...
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 671
Physicochemical properties
- Melting point
- 224 · 224-226°C
- Boiling point
- 684.8 · 684.8±55.0 °C(Predicted)
- Density
- 1.42 · 1.42
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Very Slightly, Heated), Pyridine (Slightly, Heated)
- pka
- 12.8 · 12.80±0.60(Predicted)
- form
- Solid
- color
- White to Pale Yellow
- Stability
- Hygroscopic
Chemistry & industry
Applications
UsesAtractyloside A is known to inhibit mitochondrial ADP transportation resulting in necrosis. Antimicrobial.
Additional notes
DefinitionChEBI: Atractyloside A is a terpene glycoside.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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