Smilagenin
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Smilagenin
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CAS No:
126-18-1
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Formula:
C27H44O3
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Chemical Name:
Smilagenin
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Synonyms:
Spirostan-3-ol,(3β,5β,25R)-;Smilagenin;5β-Spirostan-3β-ol,(25R)-;Spiro[8H-naphth[2′,1′:4,5]indeno[2,1-b]furan-8,2′-[2H]pyran],spirostan-3-ol deriv.;(3β,5β,25R)-Spirostan-3-ol;Isosarsasapogenin;(25R)-5β-Spirostan-3β-ol;Esmilagenin;NSC 93747;PYM 50028;Cogane
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CAS No:
Description
ChEBI: An oxaspiro compound that is(5beta,25R)-spirostan substituted by a beta-hydroxy group at position 3.
Solid
(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 an antineoplastic agent and a metabolite. It is an oxaspiro compound, a 3beta-hydroxy steroid, an organic heterohexacyclic compound and a sapogenin. It derives from a hydride of a (25R)-5beta-spirostan.|Smilagenin is a novel non-peptide, orally bioavailable neurotrophic factor inducer that readily reverses free radical neurotoxicity produced by 1-ethyl-4- phenylpyridium (MPP+) in dopaminergic neurones and reverses the decrease of neuronal growth factors and dopamine receptors in the brain. Pre-clinical work with smilagenin showed it to be neuroprotective against betya-amyloid and glutamate damage which contributes to Alzheimer's disease and reverses the changes in the area of the brain involved in Parkinson’s disease. P58 is a protein synthesis stimulant acts by restoring levels of proteins that are altered in the ageing brain, reversing the loss of nerve receptors in the ageing brain and potentially allowing for the regrowth of neural connections. P58 therefore provides a totally novel mode of action with potential importance for diseases associated with ageing of the brain. P58 is one of a family of phytochemicals isolated from traditional treatments for the elderly that have previously been shown to offer significant benefit in the treatment of senile dementia.
Characteristics
38.7
5.79380
Solid
1.0362 (rough estimate)
185 °C
474.91°C (rough estimate)
266.2ºC
1.4700 (estimate)
D25 -69° (c = 0.5 in chloroform)
207.7 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Drug Information
Investigated for use/treatment in alzheimer's disease, parkinson's disease and other neurodegenerative diseases.
Smilagenin is a novel non-peptide, orally bioavailable neurotrophic factor inducer that readily reverses free radical neurotoxicity produced by 1-ethyl-4- phenylpyridium (MPP+) in dopaminergic neurones and reverses the decrease of neuronal growth factors and dopamine receptors in the brain. P58 is a protein synthesis stimulant acts by restoring levels of proteins that are altered in the ageing brain, reversing the loss of nerve receptors in the ageing brain and potentially allowing for the regrowth of neural connections. P58 therefore provides a totally novel mode of action with potential importance for diseases associated with ageing of the brain. P58 is one of a family of phytochemicals isolated from traditional treatments for the elderly that have previously been shown to offer significant benefit in the treatment of senile dementia.
Smilagenin is a novel non-peptide, orally bioavailable neurotrophic factor inducer that readily reverses free radical neurotoxicity produced by 1-ethyl-4- phenylpyridium (MPP+) in dopaminergic neurones and reverses the decrease of neuronal growth factors and dopamine receptors in the brain.
epi-sarsasapogenin
Smilagenin Use and Manufacturing
Human drugs -> Rare disease (orphan)|Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
Computed Properties
Molecular Weight:416.6
XLogP3:6.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:416.32904526
Monoisotopic Mass:416.32904526
Topological Polar Surface Area:38.7
Heavy Atom Count:30
Complexity:694
Defined Atom Stereocenter Count:12
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Antibacterial, anti-inflammatory, detumescence, heat-clearing, diuretic, analgesic, anti-oxidant free radicals, improve body immunity
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