Deacetylanisomycin
Grundinformationen
- CAS
27958-06-1- Standard-SMILES
COc1ccc(C[C@H]2NC[C@H](O)[C@H]2O)cc1- InChIKey
UMWAPBCLJQSOJX-WOPDTQHZSA-N- Summenformel
- C12H17NO3
- Durchschnittliche Molmasse
- 223,27 g/mol
- Monoisotopische Masse
- 223,1208434
Überblick
deacetylanisomycin has been reported in Streptomyces with data available.
Namen und Bezeichner
- Bevorzugter Name
- Deacetylanisomycin
- IUPAC
- (2R,3S,4S)-2-[(4-methoxyphenyl)methyl]pyrrolidine-3,4-diol
- Englischer Name
- DEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUS
- Summenformel
- C12H17NO3
- Molmasse
- 223.27
Namen und Synonyme
Deacetylanisomycin27958-06-1Anisomycin, deacetyl-UNII-97W54EY1WU97W54EY1WU(2R,3S,4S)-2-((4-Methoxyphenyl)methyl)-3,4-pyrrolidinediol(2R,3S,4S)-2-[(4-methoxyphenyl)methyl]pyrrolidine-3,4-diol3,4-Pyrrolidinediol, 2-(p-methoxybenzyl)-, (2R,3S,4S)-(-)-DTXSID401822383,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, (2R,3S,4S)-ANISOMYCIN DEACETYLANISOMYCINANISOMYCIN DEACETYLANISOMYCIN [MI]
Weitere Namen anzeigen
SA 3097D13,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3S,4S)-
3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, (2R-(2alpha,3alpha,4beta))-3,4-PYRROLIDINEDIOL, 2-((4-METHOXYPHENYL)METHYL)-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.))-(2R,3S,4S)-2-((4-methoxyphenyl)methyl)pyrrolidine-3,4-diolRefChem:131077DTXCID50104729(-)-DeacetylanisomycinDEACETYLANISOMYCIN FROM STREPTOMYCES*GRISEOLUSorb1707394
Datenbank-Bezeichner
- CAS
27958-06-1- PubChem CID
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,3
- Polarare Oberfläche (TPSA)
- 61,7 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 216
Physikochemische Eigenschaften
- Schmelzpunkt
- 176 · 176-179°
- Siedepunkt
- 390.7 · 390.7±37.0 °C(Predicted)
- Dichte
- 1.233 · 1.233±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Methanol: soluble
- Aggregatzustand
- A solid
- pka
- 9.2 · 9.2(at 25℃)
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
- 3
Chemie und Industrie
Anwendungen
BeschreibungDeacetylanisomycin is a derivative of the protein and DNA synthesis inhibitor anisomycin with antimalarial and anticancer activity. It inhibits the growth of the P. falciparum strains K1 and T9-96 in vitro (IC50s = 40.29 and 33.57 μM, respectively). Deacetylanisomycin is cytotoxic to LU99 lung carcinoma and MCF-7 breast cancer cells (IC50s = 23 and 34 μM, respectively). It has been used as a negative control for assessment of protein synthesis inhibitor activity in molluscan neurons.
VerwendenDeacetylanisomycin is the core structure of a family of dihydroxypyrrolidines produced by several species of Streptomyces. Anisomycin esters are potent inhibitors of protein synthesis. While considered inactive, deacetylanisomycin is a potent growth regulator in plants and its underlying pharmacology is poorly researched. This is all the more significant as anisomycin undergoes facile hydrolysis to deacetylanisomycin in polar solvents in vitro, and in vivo.
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