ChemSpider 2D Image | Episilvestrol | C34H38O13

Episilvestrol

  • Molecular FormulaC34H38O13
  • Average mass654.658 Da
  • Monoisotopic mass654.231262 Da
  • ChemSpider ID9642768

  • defined stereocentres - 9 of 9 defined stereocentres

More details:

Featured data source
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1R,2R,3S,3aR,8bS)-6-({(2S,3R,6R)-6-[(1S)-1,2-Dihydroxyéthyl]-3-méthoxy-1,4-dioxan-2-yl}oxy)-1,8b-dihydroxy-8-méthoxy-3a-(4-méthoxyphényl)-3-phényl-2,3,3a,8b-tétrahydro-1H-benzo[b]cyclopenta[d]furane- 2-carboxylate de méthyle [French] [ACD/IUPAC Name]
1H-Benzo[b]cyclopenta[d]furan-2-carboxylic acid, 6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-, methyl ester, (1R,2R,3S,3aR,8bS)- [ACD/Index Name]
697235-39-5 [RN]
epi-Silvestrol
Episilvestrol
Methyl (1R,2R,3S,3aR,8bS)-6-({(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl}oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d] furan-2-carboxylate [ACD/IUPAC Name]
Methyl-(1R,2R,3S,3aR,8bS)-6-({(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl}oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d] furan-2-carboxylat [German] [ACD/IUPAC Name]
5'''-episilvestrol
furan-2-carboxylate
methyl (1R,2R,3S,3aR,8bS)-6-(((2S,3R,6R)-6-((S)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An organic heterotricyclic compound that is a 5'''-epimer of silvestrol. Isolated from <ital>Aglaia silvestris</ital>, it exhibits antineoplastic activity. ChEBI CHEBI:66485
      An organic heterotricyclic compound that is a 5'''-epimer of silvestrol. Isolated from Aglaia silvestris, it exhibits antineoplastic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66485, CHEBI:66485

    • Bio Activity:

      Apoptosis MedChem Express HY-15359
      Apoptosis inducer MedChem Express HY-15359
      Apoptosis; MedChem Express HY-15359
      Episilvestrol is a derivative of Silvestrol, which can induce apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7; 5'myc-UTR-LUC inhibtior (IC50= 0.8 nM).; IC50 value:; Target: Apoptosis inducer; in vitro: Silvestrol induced an apoptotic response, disrupted the mitochondrial trans-membrane potential and caused cytochrome c release into the cytoplasm. MedChem Express HY-15359
      Episilvestrol is a derivative of Silvestrol, which can induce apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7; 5'myc-UTR-LUC inhibtior (IC50= 0.8 nM).;IC50 value:;Target: Apoptosis inducer;In vitro: Silvestrol induced an apoptotic response, disrupted the mitochondrial trans-membrane potential and caused cytochrome c release into the cytoplasm. Immunoblot analysis indicated that, at the protein level, silvestrol produced an increase of Bcl-xl phosphorylation with a concomitant increase of bak. Furthermore, caspase-2, -9 and -10 appeared to be involved in silvestrol-mediated apoptosis. In contrast, the involvement of caspase-3 and -7 was not detected, either by immunoblot or caspase-3/-7-like activity analysis, indicating that these pathways do not play a crucial role in silvestrol-induced apoptosis [1]. The ability of silvestrol and analogues to selectively inhibit the translation of proteins with high requireme MedChem Express HY-15359

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.5±0.1 g/cm3
Boiling Point: 800.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 122.1±3.0 kJ/mol
Flash Point: 252.4±27.8 °C
Index of Refraction: 1.652
Molar Refractivity: 164.2±0.4 cm3
#H bond acceptors: 13
#H bond donors: 4
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 2
ACD/LogP: 2.32
ACD/LogD (pH 5.5): 2.15
ACD/BCF (pH 5.5): 25.32
ACD/KOC (pH 5.5): 351.77
ACD/LogD (pH 7.4): 2.15
ACD/BCF (pH 7.4): 25.32
ACD/KOC (pH 7.4): 351.74
Polar Surface Area: 172 Å2
Polarizability: 65.1±0.5 10-24cm3
Surface Tension: 72.5±5.0 dyne/cm
Molar Volume: 449.2±5.0 cm3

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