Apramycin (CHEM018337)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:09:57 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018337
Identification
Common NameApramycin
ClassSmall Molecule
DescriptionApramycin is an aminoglycoside antibiotic and has a bactericidal action against many gram-negative bacteria. Apramycin is a structurally unique antibiotic that contains a bicyclic sugar moiety and a monosubstituted deoxystreptamine. It is not approved for use in humans.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamineChEBI
4-O-(3alpha-Amino-6alpha-((4-amino-4-deoxy-alpha-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-D-streptamineChEBI
ApramicinaChEBI
ApramycineChEBI
ApramycinumChEBI
Nebramycin factor 2ChEBI
Nebramycin IIChEBI
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-a-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamineGenerator
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamineGenerator
4-O-(3a-Amino-6a-((4-amino-4-deoxy-a-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8b-hydroxy-7b-(methylamino)pyrano(3,2-b)pyran-2a-yl)-2-deoxy-D-streptamineGenerator
4-O-(3Α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamineGenerator
Apramycin sulfateMeSH
Chemical FormulaC21H41N5O11
Average Molecular Mass539.577 g/mol
Monoisotopic Mass539.280 g/mol
CAS Registry Number37321-09-8
IUPAC Name(2R,3R,4S,5S,6S)-2-{[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
Traditional Nameapramycin
SMILESCN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
InChI KeyXZNUGFQTQHRASN-XQENGBIVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminocyclitol glycosides
Alternative Parents
Substituents
  • Amino cyclitol glycoside
  • Hexose monosaccharide
  • Aminocyclitol or derivatives
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Cyclitol or derivatives
  • Monosaccharide
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Acetal
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Primary amine
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility53.3 g/LALOGPS
logP-2.8ALOGPS
logP-6.5ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area283.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.91 m³·mol⁻¹ChemAxon
Polarizability54.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mi-0609060000-be32be8bb819fe00bb8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0903010000-245a139b0e513ad0f210Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ka-6925000000-5e9c617ea15eb45bbc05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0729-2973240000-f9d27a3b85b6fc213321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-1913010000-0b9c2b857514700bb081Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114i-7920000000-fa96e884539e16c3ec58Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04626
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkApramycin
Chemspider IDNot Available
ChEBI ID2790
PubChem Compound ID3081545
Kegg Compound IDC01555
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1249675
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=340441
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=690031
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=932851