(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

• ChemBase ID: 4187
• Molecular Formular: C21H41N5O11
• Molecular Mass: 539.57714
• Monoisotopic Mass: 539.28025716
• SMILES: CN[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
• Canonical SMILES: CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
• 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

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: @apramycin
• Synonyms: Nebramycin II; Apramycin

Database IDs

• CAS Number: 37321-09-8
• PubChem SID: 46509143; 160967619
• PubChem CID: 3081545

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.28959
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -20.033087
• LogD (pH = 7.4): -12.852177
• Log P: -6.5081105
• Molar Refractivity: 120.9143 cm^3
• Polarizability: 51.61567 Å^3
• Polar Surface Area: 283.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.77
• LOG S: -1.01
• Solubility (Water): 5.33e+01 g/l

DETAILS

DrugBank - DB04626

• Drug Groups: experimental
• Description: Apramycin 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.
• Indication: For the treatment of bacterial infections in animals.
• Affected Organisms: Enteric bacteria and other eubacteria
• References: Hermann T, Tereshko V, Skripkin E, Patel DJ: Apramycin recognition by the human ribosomal decoding site. Blood Cells Mol Dis. 2007 May-Jun;38(3):193-8. Epub 2007 Jan 29. [Pubmed] ; Kondo J, Francois B, Urzhumtsev A, Westhof E: Crystal structure of the Homo sapiens cytoplasmic ribosomal decoding site complexed with apramycin. Angew Chem Int Ed Engl. 2006 May 12;45(20):3310-4. [Pubmed] ; Han Q, Zhao Q, Fish S, Simonsen KB, Vourloumis D, Froelich JM, Wall D, Hermann T: Molecular recognition by glycoside pseudo base pairs and triples in an apramycin-RNA complex. Angew Chem Int Ed Engl. 2005 Apr 29;44(18):2694-700. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Hermann T, Tereshko V, Skripkin E, Patel DJ: Apramycin recognition by the human ribosomal decoding site. Blood Cells Mol Dis. 2007 May-Jun;38(3):193-8. Epub 2007 Jan 29. Pubmed
• Kondo J, Francois B, Urzhumtsev A, Westhof E: Crystal structure of the Homo sapiens cytoplasmic ribosomal decoding site complexed with apramycin. Angew Chem Int Ed Engl. 2006 May 12;45(20):3310-4. Pubmed
• Han Q, Zhao Q, Fish S, Simonsen KB, Vourloumis D, Froelich JM, Wall D, Hermann T: Molecular recognition by glycoside pseudo base pairs and triples in an apramycin-RNA complex. Angew Chem Int Ed Engl. 2005 Apr 29;44(18):2694-700. Pubmed