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Moligand™,≥98% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Smilagenin (SMI) is a small-molecule steroidal sapogenin from Anemarrhena asphodeloides and Pelargonium hortorum widely used in traditional Chinese medicine for treating chronic neurodegeneration diseases Smilagenin (SMI) improves memory of aged rats by increasing the muscarinic receptor subtype 1 (M1)-receptor densitySmilagenin (SMI) attenuates Aβ(25-35)-induced neurodegenerationvia stimulating the gene expression of brain-derived neurotrophic factor, may represents a novel therapeutic strategy for AD
In Vitro
Smilagenin (10 μM; 24 hours) increases SH-SY5Y cell survival compared with Aβ(25-35) intoxicated cells. Smilagenin (10 μM; 24 hours) increases neurotrophic factor (GDNF) and neurotrophic factor (BDNF) mRNA level by promoting CREB phosphorylation in 1-methyl-4-phenylpyridimium (MPP + ) treated SH-SY5Y cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: SH-SY5Y cells Concentration: 10 μM Incubation Time: 24 hours Result: Elevated the SH-SY5Y cell viability. RT-PCRCell Line: SH-SY5Y cells Concentration: 10 μM Incubation Time: 24 hours Result: Increased GDNF and BDNF transcription.
In Vivo
Smilagenin (intragastric administration; 10 or 26 mg/kg, once daily; 60 days) prevents the impairment of dopaminergic neurons in chronic MPTP/probenecid-induced mouse model. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: MPTP/probenecid-induced mouse modelDosage: 10 or 26 mg/kg Administration: Intragastric administration; 10 or 26 mg/kg; once daily; 60 days Result: Ameliorated locomotor ability of MPTP/probenecid-lesioned mice.
Form:Solid
IC50& Target:mAChR1
| Canonical Smiles | CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)OC1 |
|---|---|
| IUPAC Name | (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol |
| InChIKey | GMBQZIIUCVWOCD-UQHLGXRBSA-N |
| INCHI | 1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1 |
| Isomeric SMILES | C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1 |
| Alternate CAS | 126-18-1 |
| PubChem CID | 91439 |
| NSC Number | 93747 |
| MeSH Entry Terms | epi-sarsasapogenin;epismilagenin;PYM 50028;PYM-50028;PYM50028;sarsaponin;sarsasapogenin;sarsasapogenin, (3beta,5alpha,25R)-isomer;sarsasapogenin, (3beta,5alpha,25S)-isomer;sarsasapogenin, (3beta,5beta)-isomer;sarsasapogenin, (3beta,5beta,25R)-isomer;sarsa |
| Molecular Weight | 416.64 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Triterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Triterpenoids |
| Alternative Parents | Spirostanes and derivatives 3-beta-hydroxysteroids Ketals Oxanes Tetrahydrofurans Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Hydrocarbon derivatives |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Triterpenoid - Spirostane skeleton - 3-hydroxysteroid - Hydroxysteroid - 3-beta-hydroxysteroid - Steroid - Ketal - Oxane - Tetrahydrofuran - Cyclic alcohol - Secondary alcohol - Acetal - Organoheterocyclic compound - Oxacycle - Alcohol - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
| External Descriptors | Spirostanols and derivatives |
| Solubility | Ethanol : ≥ 10 mg/mL (24.00 mM) DMSO : 5 mg/mL (12.00 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 416.600 g/mol |
| XLogP3 | 6.500 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 416.329 Da |
| Monoisotopic Mass | 416.329 Da |
| Topological Polar Surface Area | 38.700 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 694.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 12 |
| 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 |
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