(-)-Silvestrol
Grundinformationen
- CAS
697235-38-4- Standard-SMILES
COC(=O)[C@H]1[C@@H](O)[C@@]2(O)c3c(OC)cc(O[C@@H]4O[C@@H]([C@H](O)CO)CO[C@H]4OC)cc3O[C@@]2(c2ccc(OC)cc2)[C@@H]1c1ccccc1- InChIKey
GVKXFVCXBFGBCD-QKDMMWSPSA-N- Summenformel
- C34H38O13
- Durchschnittliche Molmasse
- 654,7 g/mol
- Monoisotopische Masse
- 654,23124126
Überblick
Silvestrol is an organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phenyl group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia silvestris, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a methyl ester, an ether, an organic heterotricyclic compound and a member of dioxanes.
Namen und Bezeichner
- Bevorzugter Name
- (-)-Silvestrol
- IUPAC
- methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
- Englischer Name
- (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester
- Summenformel
- C34H38O13
- Molmasse
- 654.66
Namen und Synonyme
silvestrol697235-38-4(-)-silvestrolKK3Y3KN5BVCHEBI:66484DTXSID601028120methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylatemethyl (1R,2R,3S,3aR,8bS)-6-(((2S,3R,6R)-6-((1R)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta(b)(1)benzofuran-2-carboxylateRefChem:183057DTXCID401513692Silvestrol [WHO-DD]CHEMBL555196
Weitere Namen anzeigen
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester1H-Cyclopenta[b]benzofuran-2-carboxylic acid, 6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-Methoxy-1,4-dioxan-2-yl]o xy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-Methoxy-3a-(4-Methoxypheny l)-3-phenyl-, Methyl ester, (1R,2R,3S,3aR,8bS)-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 172 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 13
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 47
- Formalladung
- 0
- Komplexität
- 1.050
Physikochemische Eigenschaften
- Schmelzpunkt
- 120 · 120-122℃
- Siedepunkt
- 800.8 · 800.8±65.0 °C(Predicted)
- Dichte
- 1.45 · 1.45
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- Soluble in DMSO
- Aggregatzustand
- Powder
- pka
- 11.57 · 11.57±0.70(Predicted)
- Farbe
- White to off-white
Chemie und Industrie
Ergänzende Hinweise
DefinitionChEBI: An organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phen l group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia si vestris, it exhibits antineoplastic activity.
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