Astromicin (CHEM016569)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:17 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016569
Identification
Common NameAstromicin
ClassSmall Molecule
DescriptionAn amino cyclitol glycoside that is L-chiro-inositol in which the hydroxy groups at positions 1, 4, and 6 are replaced by aminoacetyl)methylamino, amino, and methoxy groups, respectively, and in which the hydroxy group at position 3 is converted to the corresponding 2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranoside. The major component of fortimicin, obtained from Micromonospora olivasterospora. It is administered (as the sulfate salt) by intramuscular injection or intravenous infusion for the treatment of severe systemic infections due to sensitive Gram-negative organisms.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Amino-1-((aminoacetyl)methylamino)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolChEBI
4-Amino-1-(2-amino-N-methylacetamido)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolChEBI
Antibiotic KW-1070ChEBI
ASTMChEBI
AstromicinaChEBI
AstromicineChEBI
AstromicinumChEBI
AstromycinChEBI
Fortimicin aChEBI
KW 1070ChEBI
KW-1070ChEBI
XK 70-1ChEBI
XK-70-1ChEBI
4-Amino-1-((aminoacetyl)methylamino)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-b-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolGenerator
4-Amino-1-((aminoacetyl)methylamino)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolGenerator
4-Amino-1-(2-amino-N-methylacetamido)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-b-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolGenerator
4-Amino-1-(2-amino-N-methylacetamido)-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranosyl)-6-O-methyl-L-chiro-inositolGenerator
Abbott 44747MeSH
AstromicinMeSH
Fortimicin a sulfateMeSH
Fortimicin a sulfate (1:2)MeSH
Chemical FormulaC17H35N5O6
Average Molecular Mass405.496 g/mol
Monoisotopic Mass405.259 g/mol
CAS Registry Number55779-06-1
IUPAC Name2-amino-N-[(1S,2R,3R,4S,5S,6R)-4-amino-3-{[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy}-2,5-dihydroxy-6-methoxycyclohexyl]-N-methylacetamide
Traditional Nameastromicin
SMILES[H][C@@](C)(N)[C@]1([H])CC[C@@]([H])(N)[C@@]([H])(O[C@]2([H])[C@@]([H])(N)[C@]([H])(O)[C@]([H])(OC)[C@@]([H])(N(C)C(=O)CN)[C@@]2([H])O)O1
InChI IdentifierInChI=1S/C17H35N5O6/c1-7(19)9-5-4-8(20)17(27-9)28-15-11(21)13(24)16(26-3)12(14(15)25)22(2)10(23)6-18/h7-9,11-17,24-25H,4-6,18-21H2,1-3H3/t7-,8+,9-,11-,12-,13-,14+,15+,16+,17+/m0/s1
InChI KeyBIDUPMYXGFNAEJ-APGVDKLISA-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
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Cyclitol or derivatives
  • Oxane
  • Cyclic alcohol
  • Tertiary carboxylic acid amide
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility21.9 g/LALOGPS
logP-1.8ALOGPS
logP-4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.16ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.54 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.27 m³·mol⁻¹ChemAxon
Polarizability41.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-3149600000-aeb013286b91212fead7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-5693000000-f5cd9db638115428b975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06s9-9612000000-f88372092c9b6a05291cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1395800000-e1b24538b33e9bf01f10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-3975000000-5b0c3fa84d01de28f8bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2940000000-986dce6764bda51d8c3aSpectrum
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 IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018137
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAstromicin
Chemspider IDNot Available
ChEBI ID37923
PubChem Compound ID5284517
Kegg Compound IDC17708
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1494349
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2737953
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6526734
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6526735
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8486289