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Smilagenin

CAT: 0804-HY-106353-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-106353-01Size:5 mg
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Description
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[1]. Smilagenin (SMI) improves memory of aged rats by increasing the muscarinic receptor subtype 1 (M1) -receptor density[2]. Smilagenin (SMI) attenuates Aβ (25-35) -induced neurodegenerationvia stimulating the gene expression of brain-derived neurotrophic factor, may represents a novel therapeutic strategy for AD[3].
CAS Number
126-18-1
UNSPSC
12352005
Target
Endogenous Metabolite; mAChR
Type
Natural Products
Related Pathways
GPCR/G Protein; Metabolic Enzyme/Protease; Neuronal Signaling
Applications
Neuroscience-Neurodegeneration
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/smilagenin.html
Concentration
10mM
Purity
98.0
Solubility
DMSO : < 1 mg/mL|Ethanol : ≥ 10 mg/mL
Smiles
C[C@@H]1[C@@]2(CC[C@@H](C)CO2)O[C@]3([H])[C@@]1([H])[C@@]4([C@@]([C@@]5([H])[C@]([C@@]6([C@](C[C@@H](O)CC6)([H])CC5)C)([H])CC4)([H])C3)C
Molecular Formula
C27H44O3
Molecular Weight
416.64
References & Citations
[1]He X, et al. Smilagenin Protects Dopaminergic Neurons in Chronic MPTP/Probenecid-Lesioned Parkinson's Disease Models. Front Cell Neurosci. 2019 Feb 5;13:18.|[2]Hu Y, et al. Regulation of M1-receptor mRNA stability by smilagenin and its significance in improving memory of aged rats. Neurobiol Aging. 2010 Jun;31 (6) :1010-9.|[3]Zhang R, et al. Smilagenin attenuates beta amyloid (25-35) -induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. Neuroscience. 2012 May 17;210:275-85
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
MAChR1

Chemical Information

Smilagenin

(25R)-5beta-spirostan-3beta-ol is an oxaspiro compound that is(5beta,25R)-spirostan substituted by a beta-hydroxy group at position 3. It has a role as a metabolite and an antineoplastic agent. It is a sapogenin, a 3beta-hydroxy steroid, an oxaspiro compound and an organic heterohexacyclic compound. It derives from a hydride of a (25R)-5beta-spirostan.

CAS Number126-18-1
PubChem CID91439
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
Molecular FormulaC27H44O3
Molecular Weight416.6
XLogP6.5
Topological Polar Surface Area38.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count30
Formal Charge0
Complexity694
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
InChI
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
InChIKey
GMBQZIIUCVWOCD-UQHLGXRBSA-N
Chemical Structure
2D Structure
2D structure of Smilagenin
CAS: 126-18-1
CID: 91439
Formula: C27H44O3
MW: 416.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight416.6
XLogP36.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass416.32904526
Monoisotopic Mass416.32904526
Topological Polar Surface Area38.7 Ų
Heavy Atom Count30
Formal Charge0
Complexity694
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA5493-10Smilagenin
T4954-01SMILAGENIN ACETATE
A12599-50Smilagenin 50mg
A12599-5Smilagenin 5mg
A12599-100Smilagenin 100mg
A12599-2Smilagenin 2mg
A12599-25Smilagenin 25mg
A12599-10Smilagenin 10mg

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