(3R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid

• ChemBase ID: 73037
• Molecular Formular: C21H45N5O11S
• Molecular Mass: 575.6739
• Monoisotopic Mass: 575.28362829
• SMILES: [C@]1(C([C@H](C(OC1)O[C@@H]1C(O)C([C@H](C[C@H]1N)N)O[C@H]1O[C@@H](CC[C@H]1N)C(C)NC)O)NC)(C)O.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.CNC([C@@H]1CC[C@H]([C@H](O1)OC1[C@@H](N)C[C@H]([C@@H](C1O)OC1OC[C@](C([C@H]1O)NC)(C)O)N)N)C
• InChI: InChI=1S/C21H43N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;(H2,1,2,3,4)/t9?,10-,11+,12-,13+,14?,15-,16?,17+,18?,19-,20?,21+;/m1./s1
• InChIKey: NWQISSNHRDDWRM-UAZJPPNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
• IUPAC Traditional name: (3R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
• Synonyms: Gentacycol; Gentamicins; Gentamycinum; Gentamycin sulfate

Database IDs

• CAS Number: 1405-41-0
• PubChem SID: 162037957
• PubChem CID: 53245640

CALCULATED PROPERTIES

• Acid pKa: 12.549178
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -17.685123
• LogD (pH = 7.4): -11.792577
• Log P: -3.1371555
• Molar Refractivity: 118.0207 cm^3
• Polarizability: 49.566326 Å^3
• Polar Surface Area: 199.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: sulfate

DETAILS

Selleck Chemicals - S2472

Research Area: Infection
Biological Activity:
Gentamycin(Gentacycol) is an aminoglycoside antibiotic and was isolated from Micromonospora species. It is a broad-spectrum cell culture antibiotic that is nontoxic to viruses and mammalian cells at antibacterial and antimycoplasmal concentrations. Its extended stability and slow development of bacterial resistance allow long-term virus and tissue culture studies. It is not used for Neisseria gonorrhoeae, Neisseria meningitidis or Legionella pneumophila bacterial infections (because of the risk of the patient going into shock from lipid A endotoxin found in certain Gram-negative organisms). Gentamicin is also useful against Yersinia pestis and its relatives although need for treatment in most cases is rare, as this bacterium is the one that causes plague. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Gentamicin