(2S,3R,4S,5S,6S)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol; sulfuric acid

• ChemBase ID: 133476
• Molecular Formular: C17H36N4O14S
• Molecular Mass: 552.55114
• Monoisotopic Mass: 552.19487285
• 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)CN)O)O)N)O[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)O)N.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)O[C@@H]1[C@@H](O[C@@H]2O[C@@H](CN)[C@@H]([C@H]([C@@H]2N)O)O)[C@H](N)C[C@@H]([C@H]1O)N
• InChI: InChI=1S/C17H34N4O10.H2O4S/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17;1-5(2,3)4/h4-17,22-27H,1-3,18-21H2;(H2,1,2,3,4)/t4-,5+,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16-,17-;/m0./s1
• InChIKey: RTCDDYYZMGGHOE-NMMMDEJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6S)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol; sulfuric acid
• IUPAC Traditional name: (2S,3R,4S,5S,6S)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol; sulfuric acid
• Synonyms: Ribostamycin sulfate salt

Database IDs

• CAS Number: 53797-35-6
• EC Number: 258-783-1
• MDL Number: MFCD00057496
• PubChem SID: 162227753
• PubChem CID: 24721540

CALCULATED PROPERTIES

• Acid pKa: 12.193866
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -17.199512
• LogD (pH = 7.4): -11.747448
• Log P: -6.4305787
• Molar Refractivity: 100.172 cm^3
• Polarizability: 42.763172 Å^3
• Polar Surface Area: 262.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: WK2300000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-20/21/22
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H312-H332-H360
• GHS Precautionary statements: P201-P280-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - R2255

Application
Ribostamycin is a broad-spectrum antimicrobial isolated from Streptomyces ribosifidicus. It is used in pharmacokinetic and nephrotoxicity studies1,2.
Biochem/physiol Actions
Aminoglycosides, such as ribostamycin, bind to the bacterial 30S and 50S ribosomal subunit, which inhibits the translocation of the peptidyl-tRNA from the A-site to the P-site. This causes misreading of mRNA which makes bacteria unable to make essential proteins3. It also inhibits the chaperone activity of protein disulfide isomerase (PDI).