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32986-56-4 molecular structure
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(2S,3R,4R,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol

ChemBase ID: 133769
Molecular Formular: C18H37N5O9
Molecular Mass: 467.51448
Monoisotopic Mass: 467.25912779
SMILES and InChIs

SMILES:
C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)CO)O)N)O)O)O[C@@H]1[C@@H](C[C@@H]([C@H](O1)CN)O)N)N
Canonical SMILES:
NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@H]([C@@H]([C@H]2O)O[C@H]2O[C@H](CO)[C@H]([C@H]([C@H]2O)N)O)N)[C@@H](C[C@@H]1O)N
InChI:
InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChIKey:
NLVFBUXFDBBNBW-SNGYORCQSA-N

Cite this record

CBID:133769 http://www.chembase.cn/molecule-133769.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,3R,4R,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
IUPAC Traditional name
(2S,3R,4R,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
Synonyms
O-[3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)]-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribohexopyranosyl-(1→4)]-2-deoxy-D-streptamine
Tobramycin
CAS Number
32986-56-4
EC Number
251-322-5
MDL Number
MFCD00077885
Beilstein Number
1357507
PubChem SID
24900188
162228046
PubChem CID
16220018

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16220018 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.542545  H Acceptors 14 
H Donor 10  LogD (pH = 5.5) -20.344318 
LogD (pH = 7.4) -13.627587  Log P -6.4775004 
Molar Refractivity 106.6949 cm3 Polarizability 45.42405 Å3
Polar Surface Area 268.17 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL, clear, faintly yellow expand Show data source
RTECS
WK2100000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥99.0% (TLC) expand Show data source
Grade
certified reference material expand Show data source
Packaging
pkg of 1 g expand Show data source
Impurities
≤8% water expand Show data source
Pharmacopeia Traceability
traceable to BP 333 expand Show data source
traceable to PhEur T1500000 expand Show data source
traceable to USP 1667508 expand Show data source
Empirical Formula (Hill Notation)
C18H37N5O9 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - T4014 external link
Biochem/physiol Actions
Tobramycin is an aminoglycoside. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Spectrum of Activity: Gram negative bacteria. Not effective against Enterococci.
Tobramycin binds irreversibly to one of two aminoglycoside binding sites on the 30 S ribosomal subunit, inhibiting bacterial protein synthesis. Tobramycin may also destabilize bacterial membranes by binding to 16 S r-RNA. It inhibits translocation and elicits miscoding.
Application
Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the pseudomonas species. It is not effective against Enterococci. It is used to inhibit bacterial protein synthesis. It is used to treat pseudomonas aeruginosa lung infections and is used in combination with other antibiotics to treat urinary tract infections, gynecologic infections, peritonitis, endocarditis, pneumonia, sepsis, respiratory infections, osteomyelitis, and other soft-tissue infections. It is a potential therapy for sinus infections1.
Sigma Aldrich - 89549 external link
Biochem/physiol Actions
Tobramycin is an aminoglycoside. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Spectrum of Activity: Gram negative bacteria. Not effective against Enterococci.
Sigma Aldrich - PHR1079 external link
Biochem/physiol Actions
Tobramycin is an aminoglycoside. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Spectrum of Activity: Gram negative bacteria. Not effective against Enterococci.
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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