KAN

KANAMYCIN A

Created: 1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count69
Chiral Atom Count15
Bond Count71
Aromatic Bond Count0
2D diagram of KAN
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Chemical Component Summary

NameKANAMYCIN A
Systematic Name (OpenEye OEToolkits)(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-oxane-3,4,5-triol
FormulaC18 H36 N4 O11
Molecular Weight484.499
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O(C2C(O)C(OC1OC(CN)C(O)C(O)C1O)C(N)CC2N)C3OC(C(O)C(N)C3O)CO
SMILESCACTVS3.341NC[CH]1O[CH](O[CH]2[CH](N)C[CH](N)[CH](O[CH]3O[CH](CO)[CH](O)[CH](N)[CH]3O)[CH]2O)[CH](O)[CH](O)[CH]1O
SMILESOpenEye OEToolkits1.5.0C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N
Canonical SMILESCACTVS3.341 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
Canonical SMILESOpenEye OEToolkits1.5.0 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)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N
InChIInChI1.03 InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
InChIKeyInChI1.03 SBUJHOSQTJFQJX-NOAMYHISSA-N

Drug Info: DrugBank

DrugBank IDDB01172 
NameKanamycin
Groups
  • approved
  • vet_approved
  • investigational
DescriptionKanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.
Synonyms
  • 4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-D-glucoside
  • Kanamycin
  • Kanamycin sulfate
  • 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside
  • Kanamycin A
Brand Names
  • Kanamycin
  • Kantrex
IndicationFor treatment of infections where one or more of the following are the known or suspected pathogens: <i>E. coli</i>, <i>Proteus</i> species (both indole-positive and indole-negative), <i>E. aerogenes, K. pneumoniae, S. marcescens,</i> and <i>Acinetobacter</i> species.
Categories
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Aminoglycoside Antibacterials
  • Anti-Bacterial Agents
  • Anti-Infective Agents
ATC-Code
  • S01AA24
  • J01GB04
  • A07AA08
CAS number59-01-8

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein S12MATVNQLVRKPRARKVAKSNVPALEACPQKRGVCTRVYTTTPKKPNSALR...unknowninhibitor
16S ribosomal RNA-unknowninhibitor
Aminoglycoside 2'-N-acetyltransferaseMHTQVHTARLVHTADLDSETRQDIRQMVTGAFAGDFTETDWEHTLGGMHA...unknownsubstrate
Kanamycin nucleotidyltransferaseMNGPIIMTREERMKIVHEIKERILDKYGDDVKAIGVYGSLGRQTDGPYSD...unknownsubstrate
Aminoglycoside 3'-phosphotransferaseMSHIQRETSCSRPRLNSNLDADLYGYKWARDNVGQSGATIYRLYGKPDAP...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 6032
ChEMBL CHEMBL1384
ChEBI CHEBI:17630
CCDC/CSD KNMYSL