plazomicin   Click here for help

GtoPdb Ligand ID: 10847

Synonyms: ACHN-490 | ACHN490 | Zemdri®
Approved drug PDB Ligand
plazomicin is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Plazomicin is a semisynthetic derivative of sisomicin and belongs to the aminoglycoside class of antibacterial compounds [1].
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 16
Hydrogen bond donors 11
Rotatable bonds 14
Topological polar surface area 269.29
Molecular weight 592.34
XLogP -5.02
No. Lipinski's rules broken 3
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 NCC[C@@H](C(=O)N[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)CNCCO)O
Isomeric SMILES NCC[C@@H](C(=O)N[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)CNCCO)O
InChI InChI=1S/C25H48N6O10/c1-25(37)11-38-24(18(35)21(25)29-2)41-20-15(31-22(36)16(33)5-6-26)9-14(28)19(17(20)34)40-23-13(27)4-3-12(39-23)10-30-7-8-32/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36)/t13-,14+,15-,16+,17+,18-,19-,20+,21-,23-,24-,25+/m1/s1
InChI Key IYDYFVUFSPQPPV-PEXOCOHZSA-N
References
1. Aggen JB, Armstrong ES, Goldblum AA, Dozzo P, Linsell MS, Gliedt MJ, Hildebrandt DJ, Feeney LA, Kubo A, Matias RD et al.. (2010)
Synthesis and spectrum of the neoglycoside ACHN-490.
Antimicrob Agents Chemother, 54 (11): 4636-42. [PMID:20805391]
2. Shaeer KM, Zmarlicka MT, Chahine EB, Piccicacco N, Cho JC. (2019)
Plazomicin: A Next-Generation Aminoglycoside.
Pharmacotherapy, 39 (1): 77-93. [PMID:30511766]