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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:40:00 UTC
HMDB IDHMDB0014622
Secondary Accession Numbers
  • HMDB14622
Metabolite Identification
Common NameAmikacin
DescriptionAmikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites leading to the production of non-functional or toxic peptides. Other mechanisms not fully understood may confer the bactericidal effects of amikacin. Amikacin is also nephrotoxic and ototoxic.
Structure
Data?1582753200
Synonyms
ValueSource
1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin aChEBI
AmicacinChEBI
Amiglyde-VChEBI
AmikacinaChEBI
AmikacineChEBI
AmikacinumChEBI
AmikavetChEBI
BriclinChEBI
O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamineChEBI
AMKKegg
1-N-(L(-)-g-Amino-a-hydroxybutyryl)kanamycin aGenerator
1-N-(L(-)-Γ-amino-α-hydroxybutyryl)kanamycin aGenerator
O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-a-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamineGenerator
O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-α-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamineGenerator
Amikacin baseHMDB
Amikacin dihydrateHMDB
Amikacin sulfateHMDB
ANTIBIOTIC BB-K8HMDB
BB-K8HMDB
A.M.KHMDB
Amikacina normonHMDB
AmikafurHMDB
Amikason'sHMDB
AmikinHMDB
Bristol myers squibb brand OF amikacin sulfateHMDB
Bristol-myers squibb brand OF amikacin sulfateHMDB
Collins brand OF amikacin sulfateHMDB
Fustery brand OF amikacin sulfateHMDB
Galen brand OF amikacin sulfateHMDB
GamikalHMDB
Medical, amikacinaHMDB
Normon, amikacinaHMDB
Son's brand OF amikacin sulfateHMDB
Sulfate, amikacinHMDB
Amikacina medicalHMDB
AmikalemHMDB
AmiklinHMDB
Apothecon brand OF amikacin sulfateHMDB
BB K 8HMDB
BB-K 8HMDB
BBK 8HMDB
Norman brand OF amikacin sulfateHMDB
AmikayectHMDB
AmukinHMDB
BBK8HMDB
BiclinHMDB
BiklinHMDB
Cryopharma brand OF amikacin sulfateHMDB
Grossmann brand OF amikacin sulfateHMDB
KanbineHMDB
Lemery brand OF amikacin sulfateHMDB
Mead johnson brand OF amikacin sulfateHMDB
YectamidHMDB
BB K8HMDB
Medical brand OF amikacin sulfateHMDB
OpradHMDB
Pisa brand OF amikacin sulfateHMDB
Rovi brand OF amikacin sulfateHMDB
Chemical FormulaC22H43N5O13
Average Molecular Weight585.6025
Monoisotopic Molecular Weight585.285736487
IUPAC Name(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
Traditional Nameamikacin
CAS Registry Number37517-28-5
SMILES
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
InChI Identifier
InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
InChI KeyLKCWBDHBTVXHDL-RMDFUYIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent4,6-disubstituted 2-deoxystreptamines
Alternative Parents
Substituents
  • 4,6-disubstituted 2-deoxystreptamine
  • Gamma amino acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Fatty acyl
  • Monosaccharide
  • N-acyl-amine
  • Cyclitol or derivatives
  • Fatty amide
  • Oxane
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Primary alcohol
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 - 204 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility49.7 g/LNot Available
LogP-7.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility49.7 g/LALOGPS
logP-3.2ALOGPS
logP-8.6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area331.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity129.84 m³·mol⁻¹ChemAxon
Polarizability58.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0hh9-9803480000-4e62c20842f82ac0dc88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9400112000-f033c515f4f33f591c6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0arr-0012930000-e9e5c2d0a10606a482a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-1172910000-aa60237b3c5b04a8a3e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-4589400000-6018610d9123baec32bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-3804890000-fcfb985392039be545deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-7323930000-388eeb644330ca9e4545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-9787300000-fe9d1c5ff399b6290a43Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00479 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00479 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00479
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID34635
KEGG Compound IDC06820
BioCyc IDCPD-14197
BiGG IDNot Available
Wikipedia LinkAmikacin
METLIN IDNot Available
PubChem Compound37768
PDB IDNot Available
ChEBI ID2637
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Edson RS, Terrell CL: The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. [PubMed:10319086 ]