CHEBI:2790 - apramycin

ChEBI IDCHEBI:2790
ChEBI Nameapramycin
Stars
DefinitionAn aminoglycoside that is 2-deoxystreptamine that is substituted on the oxygen at position 4 by an (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) group.
Secondary ChEBI IDCHEBI:40708
Last Modified7 April 2011
DownloadsMolfile
FormulaC21H41N5O11
Net Charge0
Average Mass539.583
Monoisotopic Mass539.28026
SMILES[H][C@]12C[C@@H](N)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N)C[C@@H]3N)O[C@]1([H])[C@H](O)[C@H](NC)[C@@H](O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O)O2
InChIInChI=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
InChIKeyXZNUGFQTQHRASN-XQENGBIVSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug  A drug used to treat or prevent bacterial infections.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
apramycin (CHEBI:2790) has role antibacterial drug (CHEBI:36047)
apramycin (CHEBI:2790) has role antimicrobial agent (CHEBI:33281)
apramycin (CHEBI:2790) is a 2-deoxystreptamine derivative (CHEBI:61800)
apramycin (CHEBI:2790) is a aminoglycoside (CHEBI:47779)
apramycin (CHEBI:2790) is a organic heterobicyclic compound (CHEBI:27171)
IUPAC Name 
(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 4-amino-4-deoxy-α-D-glucopyranoside
INNs  Source
apramycinumChemIDplus
apramicinaChemIDplus
apramycinChemIDplus
apramycineChemIDplus
Synonyms  Source
ApramycinKEGG COMPOUND
APRAMYCINPDBeChem
4-O-(3α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5aβ,6,7,8,8aα-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamineChemIDplus
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-streptamineChemIDplus
nebramycin IIChemIDplus
nebramycin factor 2ChemIDplus
Manual XrefsDatabases
C01555KEGG COMPOUND
AM2PDBeChem
D02322KEGG DRUG
DB04626DrugBank
US3691279Patent
1743VSDB
Registry NumbersSources
Reaxys:4610404Reaxys
CAS:37321-09-8KEGG COMPOUND
CAS:37321-09-8ChemIDplus
Citations