Aureothricin
Grundinformationen
- CAS
574-95-8- Standard-SMILES
CCC(=O)Nc1c2sscc-2n(C)c1=O- InChIKey
UGZYFXMSMFMTSM-UHFFFAOYSA-N- Summenformel
- C9H10N2O2S2
- Durchschnittliche Molmasse
- 242,3 g/mol
- Monoisotopische Masse
- 242,01836991
Überblick
Aureothricin is a dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively. It is a moderate antimicrobial by-product of the thiolutin fermentation in various Streptomyces species. It has a role as an antibacterial agent, an EC 2.7.7.6 (RNA polymerase) inhibitor, an angiogenesis inhibitor and a bacterial metabolite. It is a secondary carboxamide and a dithiolopyrrolone antibiotic.
Namen und Bezeichner
- Bevorzugter Name
- Aureothricin
- IUPAC
- N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamide
- Englischer Name
- aureothricin
- Summenformel
- C9H10N2O2S2
- Molmasse
- 242.32
Namen und Synonyme
Aureothricin574-95-8propionopyrrothinepropanoyl-pyrrothineN-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamideCHEBI:1564520KX00L19Q2DTXSID60205993N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)propanamide4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one4-METHYL-6-PROPIONAMIDO-1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONEN-(4-methyl-5-oxodithiolo(4,3-b)pyrrol-6-yl)propanamide
Weitere Namen anzeigen
Propionylpyrrothione, Farcinin5-Methyl-3-propionamidopyrrolin-4-one-[4,3-d]-1,2-dithioleN-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propanamidePropanamide, N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-Propionopyrrothine, 5-Methyl-3-propionamidopyrrolin-4-one[4,3-d]-1,2-dithiole
N-(4-methyl-5-oxo-4,5-dihydro(1,2)dithiolo(4,3-b)pyrrol-6-yl)propanamideRefChem:115636DTXCID90128484N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamideN-(4-Methyl-5-oxo-4,5-dihydro-dithiolopyrrol-6-yl)propionamideN-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)propionamideN-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamideUNII-0KX00L19Q2
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,1
- Polarare Oberfläche (TPSA)
- 100 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 401
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Antibiotics
Physikochemische Eigenschaften
- Schmelzpunkt
- 260 · 260-270℃ (decomposition)
- Siedepunkt
- 479.1 · 479.1±45.0 °C(Predicted)
- Dichte
- 1.48 · 1.48±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- DMF: soluble; DMSO: soluble; Ethanol: partially soluble; Methanol: partially soluble
- pka
- 10.54 · 10.54±0.20(Predicted)
- Aggregatzustand
- Yellow to orange solid.
- Farbe
- Yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- hs_code
- 29419090
Chemie und Industrie
Anwendungen
VerwendenAureothricin is an antibiotic first described by Umezawa and co-workers in Japan in 1949. Resurgent interest in this class of microbial metabolites was stimulated by the discovery of their selective antitumour activity. Aureothricin is a more hydrophobic analogue of thiolutin, but has received only limited attention. Members of this class, notably thiolutin, are potent inhibitors of bacterial and yeast RNA polymerases, inhibitors of mannan and glucan formation in fungi, and inhibitors of tumour-cell induced angiogenesis in vivo.
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