netilmicin   Click here for help

GtoPdb Ligand ID: 12159

Synonyms: 1-N-ethylsisomicin | Sch 20569
Approved drug
netilmicin is an approved drug (FDA (1983), UK (2019))
Compound class: Synthetic organic
Comment: Netilmicin is a semisynthetic derivative of sisomicin, with activity against Gram-negative bacteria [2-3]. It belongs to the aminoglycoside class of antibacterial compounds.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 8
Rotatable bonds 8
Topological polar surface area 199.73
Molecular weight 475.3
XLogP -2.81
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCN[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)O)O[C@H]1OC(=CC[C@H]1N)CN
Isomeric SMILES CCN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]1[C@@H]([C@H]([C@@](CO1)(C)O)NC)O)O)O[C@@H]1[C@@H](CC=C(O1)CN)N)N
InChI InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
InChI Key CIDUJQMULVCIBT-MQDUPKMGSA-N
References
1. Campoli-Richards DM, Chaplin S, Sayce RH, Goa KL. (1989)
Netilmicin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use.
Drugs, 38 (5): 703-56. [PMID:2689137]
2. Miller GH, Arcieri G, Weinstein MJ, Waitz JA. (1976)
Biological activity of netilmicin, a broad-spectrum semisynthetic aminoglycoside antibiotic.
Antimicrob Agents Chemother, 10 (5): 827-36. [PMID:1008541]
3. Wright JJ. (1976)
Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic.
J. Chem. Soc., Chem. Commun.,: 206-208. DOI: 10.1039/C39760000206