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24397-89-5

24397-89-5 Structure

24397-89-5 Structure
IdentificationBack Directory
[Name]

Propanamide, 2-amino-N-(3,4,4a,5,6,7-hexahydro-5,6, 8-trihydroxy-3-met hyl-1-oxo-1H-2-benzopyran-4-yl)-
[CAS]

24397-89-5
[Synonyms]

actinobolin
(S)-N-[(3R)-3,4,4aβ,5,6,7-Hexahydro-5β,6α,8-trihydroxy-3α-methylisocoumarin-4α-yl]-2-aminopropionamide
Propanamide, 2-amino-N-(3,4,4a,5,6,7-hexahydro-5,6, 8-trihydroxy-3-met hyl-1-oxo-1H-2-benzopyran-4-yl)-
(3R)-4α-[[(S)-2-Aminopropanoyl]amino]-3,4,4aβ,5,6,7-hexahydro-5β,6α,8-trihydroxy-3α-methyl-1H-2-benzopyran-1-one
(S)-2-Amino-N-[(3R)-3,4,4aβ,5,6,7-hexahydro-5β,6α,8-trihydroxy-3α-methyl-1-oxo-1H-2-benzopyran-4α-yl]propanamide
(S)-2-Amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]propanamide
Propanamide, 2-amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-, (2S)-
[Molecular Formula]

C13H20N2O6
[MDL Number]

MFCD01718124
[MOL File]

24397-89-5.mol
[Molecular Weight]

300.31
Chemical PropertiesBack Directory
[alpha ]

D28 +59° (c = 0.5 in pH 7 phosphate buffer)
[Boiling point ]

441.54°C (rough estimate)
[density ]

1.2243 (rough estimate)
[refractive index ]

1.5430 (estimate)
[pka]

7.5, 8.8(at 25℃)
Hazard InformationBack Directory
[Uses]

Actinobolin ((+)-Actinobolin) is an antibiotic, that inhibits protein synthesis by targeting bacterial and eukaryotic ribosomes. Actinobolin inhibits Mycobacterium smegmatis, Escherichia coli and rabbit reticulocyte lysate (RRL) with an IC50 of 19.2, 27.9, and 288 μmol/L, respectively[1].
[References]

[1] Tharra PR, et al., Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202116520. DOI:10.1002/anie.202116520
Safety DataBack Directory
[Toxicity]

LD50 in mice, rats (mg/kg): 800 ±27, 1550 ±26 i.v. (Pittillo)
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