Compound ID | 2696

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Purpuromycin

Class: Protein synthesis inhibitor

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Inhibits aminoacyl-tRNA formation by directly interacting with the tRNA inactivating its capacity to be aminoacylated
Target Pathogen: Active against Staphylococcus aureus, MDR Staphylococcus aureus, Streptococcus haemolyticus, Streptococcus pneumoniae, Clostridium perfringens, Proteus vulgaris, and Escherichia coli
Description: Natural product from Actinoplanes ianthinogenes; contains naphthazarin and isocoumarin moieties; has very poor solubility, binds to proteins, and inactivated in serum
Institute where first reported: Research Laboratories, Gruppo Lepetit S. p. A., Via Durando, 38, Milano, Italy
Year first mentioned: 1974
Development status: Experimental
Chemical structure(s):
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Molecular weight: 538.41
Iso. SMILES: COC1=C(C2=C(C(=C1)O)C(=O)C3=C(C2=O)O[C@]4(C3)C[C@@H](C5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O)O
InChI Key: DJICBKSAAXLOMR-GWQKEKGPSA-N
Can. SMILES: COC1=CC(=C2C(=C1O)C(=O)C3=C(C[C@]4(C[C@@H](C5=CC6=C(C(=C5O4)O)C(=O)OC(=C6)C(=O)OC)O)O3)C2=O)O
InChI: InChI=1S/C26H18O13/c1-35-13-5-11(27)16-17(19(13)30)21(32)23-10(18(16)29)6-26(39-23)7-12(28)9-3-8-4-14(24(33)36-2)37-25(34)15(8)20(31)22(9)38-26/h3-5,12,27-28,30-31H,6-7H2,1-2H3/t12-,26+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/substance/386993668
Citations:
  • https://rnajournal.cshlp.org/content/3/8/905.long
  • https://www.jstage.jst.go.jp/article/antibiotics1968/27/3/27_3_161/_article

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