(2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 73029
• Molecular Formular: C41H68O14
• Molecular Mass: 784.97022
• Monoisotopic Mass: 784.46090686
• SMILES: [C@@H]1([C@@H]([C@H]([C@@H](OC1)O[C@@H]1C([C@H]2[C@]3(CC1)[C@]1([C@@H](C[C@@H]2O[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)CO)[C@]2([C@](CC1)([C@H]([C@H](C2)O)[C@@]1(CC[C@@H](O1)C(C)(C)O)C)C)C)C3)(C)C)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@]4([C@@]5([C@@H]2C(C)(C)[C@H](CC5)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)C4)CC[C@]2([C@@]3(C)C[C@@H]([C@@H]2[C@]2(C)CC[C@@H](O2)C(O)(C)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19-,20+,21-,22+,23-,24-,25+,26-,27+,28-,29+,30+,31-,32-,33-,34+,37+,38-,39-,40-,41+/m0/s1
• InChIKey: QMNWISYXSJWHRY-AUJDEUPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Cyclosiversioside F; Astragaloside A

Database IDs

• CAS Number: 83207-58-3
• PubChem SID: 162037949
• PubChem CID: 13943299

CALCULATED PROPERTIES

• Acid pKa: 11.925284
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -0.3115432
• LogD (pH = 7.4): -0.31155598
• Log P: -0.31154302
• Molar Refractivity: 194.5801 cm^3
• Polarizability: 79.65742 Å^3
• Polar Surface Area: 228.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2415

Research Area: Metabolic Disease
Biological Activity:
Astragaloside A is a pure small molecular compound isolated from Radix Astragali and is commonly used in the treatment of degenerative bone diseases such as osteoporosis. Astragaloside A plus 500 rpm for 3 days and Astragaloside A plus 200 rpm for 5 days markedly decreased osteogenesis the expression of associated protein and gene. [1] Astragaloside A would increase osteogenesis when cells of preosteoblast OCT-1 were subjected to proper centrifugating pressure and a pertinent period of time.In addition, it was reported that Astragaloside A had a potent preventive action on myocardial fibrosis in CVB3-induced dilated cardiomyopathy that might be due to downregulation of TGF-β1-Smad signaling. [2] In another study, ferulic acid significantly prevented IL-1β-induced JNK phosphorylation, without affecting ERK or P38 phosphorylation. Neither AS-IV nor FA alone had any effect on the cells. [3]

REFERENCES

• Bian Q et al. Pharmazie. 2011 Jan;66(1):63-8.