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基本情報
- CAS
126-18-1- 標準SMILES
C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
GMBQZIIUCVWOCD-UQHLGXRBSA-N- 分子式
- C27H44O3
- 平均分子量
- 416.6 g/mol
- 単同位体質量
- 416.32904526
名称と識別子
- 優先名称
- Smilagenin
- IUPAC
- (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
- 現地名
- (25R)-5β-スピロスタン-3β-オール
- 英語名
- SMILAGENIN
- 分子式
- C27H44O3
- 分子量
- 416.64
名称と別名
Smilagenin126-18-1Isosarsapogenin(25R)-5beta-Spirostan-3beta-olIsosarsasapogeninEsmilageninCogane(25R)-Spirostan-3beta-olGQE3Q7YMVZNSC-93747CHEBI:28933DTXSID301026551
名称をさらに表示
イソサルササポゲニンスミラゲニン(25R)-5β-スピロスタン-3β-オール(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-テトラメチル-5'-オキサスピロ[オキサン-2,6'-ペンタシクロ[10.8.0.02,9.04,8.013,18]イコサン]-16'-オールNsc93747PYM50028AI3-44895PYM 50028Smilax china L
(3beta,5beta,25R)-spirostan-3-ol(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-olesmilageninasmilageninesmilageninum(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-olRefChem:183409DTXCID701510716
データベース識別子
- CAS
126-18-1
物性
構造計算による物性補完中
- XLogP
- 6.5
- 極性表面積
- 38.7 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 694
実験および物理化学的性質
Melting Point185 °C
Physical DescriptionSolid
Collision Cross Section
207.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
203.83 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；199.87 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 185 °C · ~185 °C
- 比旋光度
- 25 · D25 -69° (c = 0.5 in chloroform)
- 沸点
- 474.91 °C · 474.91°C (rough estimate)
- 比重(密度)
- 1.0362 · 1.0362 (rough estimate)
- 屈折率
- 1.47 · 1.4700 (estimate)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 10 mg/mL · Ethanol: ≥ 10 mg/mL (24.00 mM); DMSO: < 1 mg/mL (insoluble or slightly soluble)
- 外見
- Solid
- 酸解離定数(Pka)
- 15.14 · 15.14±0.70(Predicted)
- 色
- White to off-white
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- F
- 10
- wgk
- 3
化学と産業
薬理情報
Pharmacodynamics
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.
Mechanism of Action
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.
Cellular LocationsExtracellular；Membrane
調製方法
純化方法Chromatograph smilagenin on active Al2O3 and elute with *C6H6, then recrystallise it from Me2CO, aqueous EtOH (m 187-188o) or MeOH. The acetate crystallises from MeOH with m 152o and [] D 25 -59.6o, [] 546 25 –68.9o (c 0.25, CHCl3). [Askew J Chem Soc 1399 1936 and 1402 1936, Scheer et al. J Am Chem Soc 77 6411955, Beilstein 19 III/IV 826.]
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