vertilmicin   Click here for help

GtoPdb Ligand ID: 11018

Compound class: Synthetic organic
Comment: Vertilmicin is a semisynthetic aminoglycoside antibacterial that inhibits bacterial growth by inhibiting protein synthesis. It has Gram-negative and Gram-positive activity [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 12
Hydrogen bond donors 8
Rotatable bonds 8
Topological polar surface area 199.73
Molecular weight 489.32
XLogP -2.29
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)C(N)C
Isomeric 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)C(N)C
InChI InChI=1S/C22H43N5O7/c1-5-27-13-8-12(25)17(33-20-11(24)6-7-14(32-20)10(2)23)15(28)18(13)34-21-16(29)19(26-4)22(3,30)9-31-21/h7,10-13,15-21,26-30H,5-6,8-9,23-25H2,1-4H3/t10?,11-,12+,13-,15+,16-,17-,18+,19-,20-,21-,22+/m1/s1
InChI Key QVRLHIRFLRXFIW-OFMFRWEUSA-N
References
1. Li CR, Yang XY, Lou RH, Zhang WX, Wang YM, Yuan M, Li Y, Chen HZ, Hong B, Sun CH et al.. (2008)
In vitro antibacterial activity of vertilmicin and its susceptibility to modifications by the recombinant AAC6'-APH2'' enzyme.
Antimicrob Agents Chemother, 52 (11): 3875-82. [PMID:18710917]
2. You XF, Li CR, Yang XY, Yuan M, Zhang WX, Lou RH, Wang YM, Li GQ, Chen HZ, Song DQ et al.. (2009)
In vivo antibacterial activity of vertilmicin, a new aminoglycoside antibiotic.
Antimicrob Agents Chemother, 53 (10): 4525-8. [PMID:19635958]