dibekacin   Click here for help

GtoPdb Ligand ID: 12134

Synonyms: 3',4'-dideoxykanamycin B | debecacin
Approved drug PDB Ligand
dibekacin is an approved drug
Compound class: Synthetic organic
Comment: Dibekacin is a semisynthetic derivative of bekanamycin (kanamycin B), with activity against Gram-positive and Gram-negative bacteria [1]. It belongs to the aminoglycoside class of antibacterial compounds.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 13
Hydrogen bond donors 9
Rotatable bonds 6
Topological polar surface area 247.94
Molecular weight 451.26
XLogP -4.78
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES NC[C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)N)N
Isomeric SMILES C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)N)N)N
InChI InChI=1S/C18H37N5O8/c19-4-6-1-2-7(20)17(28-6)30-15-8(21)3-9(22)16(14(15)27)31-18-13(26)11(23)12(25)10(5-24)29-18/h6-18,24-27H,1-5,19-23H2/t6-,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChI Key JJCQSGDBDPYCEO-XVZSLQNASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
(2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
International Nonproprietary Names Click here for help
INN number INN
3610 dibekacin
Synonyms Click here for help
3',4'-dideoxykanamycin B | debecacin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Dibekacin
Other databases
CAS Registry No. 34493-98-6 (source: Scifinder)
ChEBI CHEBI:37945
ChEMBL Ligand CHEMBL560976
DrugBank Ligand DB13270
DrugCentral Ligand 855
GtoPdb PubChem SID 472319256
PubChem CID 470999
RCSB PDB Ligand 84D
Search Google for chemical match using the InChIKey JJCQSGDBDPYCEO-XVZSLQNASA-N
Search Google for chemicals with the same backbone JJCQSGDBDPYCEO
Search PubMed clinical trials dibekacin
Search PubMed titles dibekacin
Search PubMed titles/abstracts dibekacin
UniChem Compound Search for chemical match using the InChIKey JJCQSGDBDPYCEO-XVZSLQNASA-N
UniChem Connectivity Search for chemical match using the InChIKey JJCQSGDBDPYCEO-XVZSLQNASA-N