Compound ID | 668

Update compound information

Actinonin

Synonym(s): VRC 483  |  VRC-483  |  VRC483

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Peptide deformylase inhibitor
Target Pathogen: Active against Staphylococcus aureus and Haemophilus influenzae
Description: Natural product from Streptomyces sp.; a hydroxamic acid pseudopeptide; Margolis P, Hackbarth C, Lopez S, et al. Resistance to deformylase inhibitor VRC484 is caused by mutations in formyl transferase. 39th-ICAAC 1999;333.
Institute where first reported: Versicor (Pfizer, USA)
Year first mentioned: 1999
Development status: Experimental
Reason dropped: Taken forward into clinical trials for other conditions including angiogenesis; high frequency selection of resistant Staphylococcus aureus mutants
Chemical structure(s):
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Molecular weight: 385.5
Iso. SMILES: CCCCC[C@H](CC(=O)NO)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1CO
InChI Key: XJLATMLVMSFZBN-VYDXJSESSA-N
Can. SMILES: CCCCC[C@H](CC(=O)NO)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1CO
InChI: InChI=1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24)/t14-,15+,17+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/443600
Citation: https://doi.org/10.1038/195701b0

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