Azadiradione
Grundinformationen
- CAS
26241-51-0- Standard-SMILES
CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC(=O)[C@H]3c3ccoc3)[C@@]21C- InChIKey
KWAMDQVQFVBEAU-HMWIRDDCSA-N- Summenformel
- C28H34O5
- Durchschnittliche Molmasse
- 450,6 g/mol
- Monoisotopische Masse
- 450,24062418
Überblick
Azadiradione is a tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities. It has a role as an antimycobacterial drug, an anti-inflammatory agent and a plant metabolite. It is a member of furans, a tetracyclic triterpenoid, a cyclic terpene ketone, a limonoid and an acetate ester.
Namen und Bezeichner
- Bevorzugter Name
- Azadiradione
- IUPAC
- [(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
- Englischer Name
- (13α,17α)-7α-Acetoxy-21,23-epoxy-4,4,8-trimethyl-24-nor-5α-chola-1,14,20,22-tetrene-3,16-dione
- Summenformel
- C28H34O5
- Molmasse
- 450.58
Namen und Synonyme
Azadiradione26241-51-0CHEBI:67280[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate((5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta(a)phenanthren-7-yl) acetateRefChem:115927Azadiradione (~90%)(5a,7a,13a,17a)-7-(Acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24-norchola-1,14,20,22-tetraene-3,16-dioneorb1218251orb1297018CHEMBL1215754SCHEMBL29398035
Weitere Namen anzeigen
AZADIRADIONE(P)Azadiradione, 10 mM in DMSO(13α,17α)-7α-Acetoxy-21,23-epoxy-4,4,8-trimethyl-24-nor-5α-chola-1,14,20,22-tetrene-3,16-dione24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5α,7α,13α,17α)-anti-nociceptive,antimycobacterial,Inhibitor,Heat shock proteins,inhibit,HSF1 Activator,Azadiradione,HSP,anti-inflammatory activities,bioactive limonoid
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 73,6 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 975
Physikochemische Eigenschaften
- Schmelzpunkt
- 99 °C · >99°C (dec.)
- Siedepunkt
- 552.1 · 552.1±50.0 °C(Predicted)
- Dichte
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- Farbe
- Pale Beige
- Biologische Quelle
- plant
- Wasserlöslichkeit
- water: slightly soluble
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- KWAMDQVQFVBEAU-BQDUOGPESA-N
- SMILES
- [o]1cc(cc1)[C@H]2[C@@]3(CC[C@@H]4[C@@]5([C@@H](C[C@H](C4(C3=CC2=O)C)OC(=O)C)C(C(=O)C=C5)(C)C)C)C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Ergänzende Hinweise
DefinitionChEBI: A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimyc bacterial and anti-inflammatory activities.
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