kanamycin B

Also known as 2'-amino-2'-deoxykanamycin, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1->6))-2-deoxy-D-streptamine, Nebramycin V, bekanamycin

Bekanamycin (INN; kanamycin B) is an aminoglycoside antibiotic.

In the Vinony graph

Vinony's link graph records 111 inbound references to kanamycin B, and connects out to neomycin, antibiotic and chemical formula.

It is catalogued under topics including Aminoglycoside antibiotics, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.

Vinony links it to 11 Wikipedia language editions.

Chemical data

Formula: C18H37N5O10
Molecular weight: 483.5 g/mol
IUPAC name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol
SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
InChIKey: SKKLOUVUUNMCJE-FQSMHNGLSA-N
XLogP: -7.2
Polar surface area: 288 Å²
H-bond donors: 11
H-bond acceptors: 15
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: osteomyelitis, bacterial disease

via ChEMBL · EBI

Research

159 papers

Genome-wide identification of Kanamycin B binding RNA in Escherichia coli.BMC genomics · 2023
HPLC-ELSD determination of kanamycin B in the presence of kanamycin A in fermentation broth.Biomedical chromatography : BMC · 2015
Construction of kanamycin B overproducing strain by genetic engineering of Streptomyces tenebrarius.Applied microbiology and biotechnology · 2011
Transcriptome profiling in response to Kanamycin B reveals its wider non-antibiotic cellular function in Escherichia coli.Frontiers in microbiology · 2022
Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering.PloS one · 2017

via PubMed

Wikidata facts

Part of: kanamycin (extract)
Mass: 483.254

Show 4 more facts

chemical formula: C₁₈H₃₇N₅O₁₀
canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
subject has role: antibiotic

Sources (2)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

References

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461747587 | IUPAC_name = (2S,3R,4S,5S,6R)-4-amino-2-{[(2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol | image = Bekanamycin.png | image_class = skin-invert-image

Excerpted from Wikipedia’s “kanamycin B” article, available under the CC BY-SA 4.0 licence.