(2S,3S)-2,3-Dihydroxy-3-[(6S)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl benzoate
Grundinformationen
- CAS
37134-40-0- Standard-SMILES
C=C1CCOC2([C@@H](O)[C@@](C)(O)COC(=O)c3ccccc3)NC(=O)[C@]1(O)NC2=O- InChIKey
YYGLCPHONATYBU-CTQCHYAJSA-N- Summenformel
- C19H22N2O8
- Durchschnittliche Molmasse
- 406,4 g/mol
- Monoisotopische Masse
- 406,13761566
Namen und Bezeichner
- Bevorzugter Name
- (2S,3S)-2,3-Dihydroxy-3-[(6S)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl benzoate
- IUPAC
- [(2S,3S)-2,3-dihydroxy-3-[(6S)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl] benzoate
- Englischer Name
- BicozaMycin benzoate, FR 2054
- Summenformel
- C19H22N2O8
- Molmasse
- 406.39
Namen und Synonyme
DTXSID50190622(2S,3S)-2,3-Dihydroxy-3-[(6S)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl benzoateFR2054BicycloMycin benzoateBicyclomycin benzoate,FR 2054BicozaMycin benzoate, FR 2054Bicyclomycin, 3'-benzoate (9CI)Bicyclomycin benzoate (Synonyms: FR2054)(2S,3S)-2,3-dihydroxy-3-((1S,6R)-6-hydroxy-5-methylene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl)-2-methylpropyl benzoate
Datenbank-Bezeichner
- CAS
37134-40-0- PubChem CID
- 71587135
- DTXSID
DTXSID50190622
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 154 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 721
Physikochemische Eigenschaften
- Schmelzpunkt
- 123 °C · >123°C (dec.)
- Siedepunkt
- 788.6 · 788.6±60.0 °C(Predicted)
- Dichte
- 1.49 · 1.49±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 9.82 · 9.82±0.60(Predicted)
- Farbe
- White
Chemie und Industrie
Anwendungen
VerwendenBicozaMycin benzoate, FR 2054 is a polar metabolite first isolated from Streptomyces sapporonensis in 1972, with activity against Gram negative bacteria. The selective Gram negative profile of bicyclomycin is rare among Streptomyces metabolites, and in an effort to overcome its poor in vivo absorption, the benzoate ester was prepared by reaction with the more exposed primary alcohol. BicozaMycin benzoate, FR 2054 benzoate has limited use as a veterinary antibiotic.
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