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(2S,3R,4S,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; sulfuric acid
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ChemBase ID:
132748
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Molecular Formular:
C18H39N5O13S
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Molecular Mass:
565.59296
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Monoisotopic Mass:
565.22650733
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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.OS(=O)(=O)O
Canonical SMILES:
OS(=O)(=O)O.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.H2O4S/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;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1
InChIKey:
ZEUUPKVZFKBXPW-TWDWGCDDSA-N
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Cite this record
CBID:132748 http://www.chembase.cn/molecule-132748.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(2S,3R,4S,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; sulfuric acid
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IUPAC Traditional name
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sulfuric acid; tobramycin
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Synonyms
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Tobramycin sulfate salt
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Tobramycin sulfate salt 硫酸盐
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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12.542545
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H Acceptors
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14
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H Donor
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10
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LogD (pH = 5.5)
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-20.344318
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LogD (pH = 7.4)
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-13.627587
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Log P
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-6.4775004
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Molar Refractivity
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106.6949 cm3
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Polarizability
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45.42405 Å3
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Polar Surface Area
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268.17 Å2
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Rotatable Bonds
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6
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Lipinski's Rule of Five
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false
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DETAILS
DETAILS
Sigma Aldrich
Sigma Aldrich -
T1783
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Biochem/physiol Actions Tobramycin sulfate 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. Tobramycin binds to an RNA aptamer, which is structurally similar to the A site of 16S rRNA2. 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 at the level of 30S (16S rRNA) and 70S ribosomal complex assembly. 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. Product T1783 has been used to study antibiotic resistance2. |
PATENTS
PATENTS
PubChem Patent
Google Patent