CHEBI:2790 - apramycin

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ChEBI Name apramycin
ChEBI ID CHEBI:2790
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40708
Supplier Information
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Formula C21H41N5O11
Net Charge 0
Average Mass 539.57710
Monoisotopic Mass 539.280
InChI InChI=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
InChIKey XZNUGFQTQHRASN-XQENGBIVSA-N
SMILES [H][C@]12C[C@@H](N)[C@@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)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
Roles Classification
Biological Role(s): 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(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
apramicina ChemIDplus
apramycin ChemIDplus
apramycine ChemIDplus
apramycinum ChemIDplus
Synonyms Sources
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-streptamine ChemIDplus
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-streptamine ChemIDplus
APRAMYCIN PDBeChem
Apramycin KEGG COMPOUND
nebramycin factor 2 ChemIDplus
nebramycin II ChemIDplus
Manual Xrefs Databases
1743 VSDB
AM2 PDBeChem
C01555 KEGG COMPOUND
D02322 KEGG DRUG
DB04626 DrugBank
US3691279 Patent
View more database links
Registry Numbers Types Sources
37321-09-8 CAS Registry Number KEGG COMPOUND
37321-09-8 CAS Registry Number ChemIDplus
4610404 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1249675 PubMed citation Europe PMC
340441 PubMed citation Europe PMC
690031 PubMed citation Europe PMC
932851 PubMed citation Europe PMC
Last Modified
07 April 2011
General Comment
2011-04-07 Apramycin is a structurally unique antibiotic produced by a strain of Streptomyces tenebrarius, containing a bicyclic sugar moiety and a monosubstituted deoxystreptamine. An aminoglycoside antibiotic, it has bactericidal activity against many Gram-negative bacteria and is used in veterinary medicine, but is not approved for use in humans.