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Apramycin (Nebramycin II)

CAT: 0931-T38303Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0931-T38303Size:500 mg
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CAS Number
37321-09-8
Target
Antibiotic, Antibacterial, Others
Related Pathways
Microbiology/Virology, Others
Bioactivity
Apramycin (Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine.Target: Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria.
Smiles
[H][C@]1(O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@]3([H])[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@]2([H])[C@H](O)[C@@H]1NC
Molecular Formula
C21H41N5O11
Molecular Weight
539.58
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Apramycin

Apramycin is 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-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl) group. It has a role as an antimicrobial agent and an antibacterial drug. It is an organic heterobicyclic compound, an aminoglycoside and a 2-deoxystreptamine derivative.

CAS Number37321-09-8
PubChem CID3081545
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)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol
Molecular FormulaC21H41N5O11
Molecular Weight539.6
XLogP-7
Topological Polar Surface Area284
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Heavy Atom Count37
Formal Charge0
Complexity760
SMILES
CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O
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
Chemical Structure
2D Structure
2D structure of Apramycin
CAS: 37321-09-8
CID: 3081545
Formula: C21H41N5O11
MW: 539.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight539.6
XLogP3-7
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Exact Mass539.28025714
Monoisotopic Mass539.28025714
Topological Polar Surface Area284 Ų
Heavy Atom Count37
Formal Charge0
Complexity760
Isotope Atom Count0
Defined Atom Stereocenter Count17
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
GTR19190022-01Apramycin (Nebramycin II)
GTR19266091-01Nebramycin V’
GTR19255434-01Nebramycin IV
MBS3604288-01Apramycin
AR-T02420-01Tobramycin (Nebramycin) Impurity
B1665-50Apramycin Sulfate
HY-17558RApramycin (Standard)
377036Apramycin discontinued

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