D-erythro-Eritadenine
eritadenine · AA-307 · Lentysine · lentinacin · D-ERITADENINE · d-erythronicaci · 4-(6-AMinopurin-9-yl)-4-deoxy-D-erythronic Acid · 4-(9-Adenyl)-D-erythro-2,3-dihydroxybutyric acid
Identifikatoren & physikalische Daten
| CAS No. | 23918-98-1 |
|---|---|
| Summenformel | C9H11N5O4 |
| Durchschnittliche Molmasse | 253,22 g/mol |
| Monoisotopische Masse | 253,08110385 g/mol |
| SMILES | Nc1ncnc2c1ncn2CC(O)C(O)C(=O)O |
| InChIKey | LIEMBEWXEZJEEZ-UHFFFAOYSA-N |
| PubChem CID | 2933 |
| ChEBI | CHEBI:179057 |
Chemische & physikalische Eigenschaften
| XLogP | -1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 147 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 317 |
| Schmelzpunkt | 261 - 263 °C>270°C (dec.) |
| Physical Description | Solid |
| Siedepunkt | 721℃ |
| Dichte | 1.92 |
| Brechungsindex | 1.7610 (estimate) |
| Flammpunkt | 390℃ |
| Lagerbedingungen | Refrigerator |
| Löslichkeit | Aqueous Acid (Slightly, Heated), DMSO (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 3.37±0.17(Predicted) |
| Farbe | White to Light Beige |
Anwendungen & Verwendung
Beschreibung
The empirical formula of this alkaloid should read C9H II N 504' The natural compound is the D-Erythro-form of the base. Melting points recorded for this alkaloid are 279°C (dec.) by Kamiya et al and 26l-3°C (dec.) by Chibata and his colleagues. The alkaloid has specific rotations of [α]D+ 16° (N-HC1) and [α] D + 50° (0.1 N-NaOH). It gives an ultraviolet spectrum in H20 with a single absorption maximum at 26l.5 nm which is shifted to 259.5 nm inN-HCl and is at 262 nm in N-NaOH. Eritadenine forms a methyl ester, m.p. 231°C (dec.) and a diacetate, m.p. 225°C (dec.).
Verwenden
Hypocholesterolemic isolated from shiitake mushrooms, effecting phospholipid and linoleic acid metabolisms. Specifically, Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.