Compound ID | 3005

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eAmSPC 2593

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Mycobacterium abscessus, Mycobacterium tuberculosis, Mycobacterium avium, Streptococcus sp., methicillin-resistant Staphylococcus aureus, and Escherichia coli; protein synthesis inhibitor
Description: Semisynthetic compound; derived from spectinomycin (N-ethylene linked aminomethyl spectinomycin); shows synergistic effect with clarithromycin, linezolid, bedaquiline, and clofazimine; efficacious in reducing bacterial burden in Mycobacterium abscessus infection in immunocompromised mouse
Institute where first reported: Department of Chemical Biology and Therapeutics, St. Jude Children’s Research Hospital, Memphis
Year first mentioned: 2024
Development status: Experimental
Chemical structure(s):
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Molecular weight: 485.55
Iso. SMILES: C[C@@H]1C[C@]([C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O)(CNCCC4=CC=C(C=C4)F)O
InChI Key: KRCLSDQUEUBIKY-LLHOOWCXSA-N
Can. SMILES: C[C@@H]1C[C@@](CNCCC2=CC=C(C=C2)F)([C@]3([C@@H](O1)O[C@@H]4[C@H]([C@@H]([C@@H]([C@@H]([C@H]4O3)NC)O)NC)O)O)O
InChI: InChI=1S/C23H36FN3O7/c1-12-10-22(30,11-27-9-8-13-4-6-14(24)7-5-13)23(31)21(32-12)33-20-18(29)15(25-2)17(28)16(26-3)19(20)34-23/h4-7,12,15-21,25-31H,8-11H2,1-3H3/t12-,15-,16+,17+,18+,19-,20-,21+,22-,23-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/117986569
Guide to Pharmacology: eAmSPC 2593
Citation: https://www.pnas.org/doi/10.1073/pnas.2314101120

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