BEKANAMYCIN

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Search structure


Synonyms	Aminodeoxykanamycin Bekanamycin Bekanamycin sulfate Kanamycin b Kantrex Klebcil NK 1006 NK-1006 Nebramycin v
Status
Molecule Category	UNKNOWN
ATC	J01GB13
UNII	15JT14C3GI
EPA CompTox	DTXSID8023185


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	SKKLOUVUUNMCJE-FQSMHNGLSA-N
Smiles	NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O
InChI	InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H37N5O10
Molecular Weight	483.52
AlogP	-7.33
Hydrogen Bond Acceptor	15.0
Hydrogen Bond Donor	11.0
Number of Rotational Bond	6.0
Polar Surface Area	288.4
Molecular species	BASE
Aromatic Rings	0.0
Heavy Atoms	33.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial 70S ribosome inhibitor	INHIBITOR	PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme	-	5600	-	-	-

Assay Description	Organism	Bioactivity	Reference
Tested for binding affinity against RNA construct E	None	910.0 nM
Binding affinity to A-site RNA	None	60.0 nM
Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by MTT method	Bacillus subtilis	0.39 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 6538 after 24 hrs by MTT method	Staphylococcus aureus	1.562 ug.mL-1
Antibacterial activity against Escherichia coli ATCC 35218 after 24 hrs by MTT method	Escherichia coli	3.125 ug.mL-1
Antibacterial activity against Pseudomonas aeruginosa ATCC 13525 after 24 hrs by MTT method	Pseudomonas aeruginosa	3.125 ug.mL-1
Binding affinity to Escherichia coli 16S rRNA helix 44 assessed as stabilization of classical state occupancy by tRNA by smFRET	Escherichia coli	300.0 nM
Binding affinity to Escherichia coli 23S rRNA assessed as stabilization of classical state occupancy by tRNA by smFRET	Escherichia coli	300.0 nM
Cytotoxicity against HEK293 cells measured after 24 hrs by MTT assay	Homo sapiens	500.0 ug.mL-1
Binding affinity to 16S rRNA A-site in Escherichia coli S30 extract assessed as inhibition of translation measured after 30 mins by coupled transcription/translation-based luciferase reporter gene assay	Escherichia coli	40.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	28098
ChEMBL	CHEMBL176
DrugBank	DB13673
DrugCentral	1520
FDA SRS	15JT14C3GI
KEGG	C00825
PDB	9CS
PubChem	439318
SureChEMBL	SCHEMBL158426
ZINC	ZINC000053132258

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).