bis(1-[(1S,2S,3R,4S,5S,6R)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)

• ChemBase ID: 119516
• Molecular Formular: C42H88N14O36S3
• Molecular Mass: 1461.41532
• Monoisotopic Mass: 1460.46477821
• SMILES: [C@H]1([C@@]([C@@H](O[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)C)(O)CO)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC.[C@H]1([C@@]([C@@H](O[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)C)(O)CO)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC.S(=O)(=O)(O)O.S(=O)(=O)(O)O.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@H]([C@@H]([C@H]3NC(=N)N)O)NC(=N)N)O[C@H]([C@]2(O)CO)C)[C@H]([C@@H]([C@H]1O)O)NC.OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@H]([C@@H]([C@H]3NC(=N)N)O)NC(=N)N)O[C@H]([C@]2(O)CO)C)[C@H]([C@@H]([C@H]1O)O)NC
• InChI: InChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;;/m00.../s1
• InChIKey: CZWJCQXZZJHHRH-YZTFXSNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(1-[(1S,2S,3R,4S,5S,6R)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine); tris(sulfuric acid); bis(1-[(1R,2S,3S,4R,5S,6S)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• IUPAC Traditional name: bis(1-[(1S,2S,3R,4S,5S,6R)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine); tris(sulfuric acid); bis(1-[(1R,2S,3S,4R,5S,6S)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• Synonyms: 1,1'-((1S,2S,3R,4S,5S,6R)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-4-(hydroxymethyl)-5-methyltetrahydrofuran-2-yl)o xy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine se squisulfate; Dihydrostreptomycin sesquisulfate

Database IDs

• CAS Number: 5490-27-7
• EC Number: 226-823-7
• MDL Number: MFCD00070252
• Beilstein Number: 3894221
• PubChem SID: 24894093; 24893928; 162103197
• PubChem CID: 6419912

CALCULATED PROPERTIES

• Acid pKa: 12.219626
• H Acceptors: 19
• H Donor: 15
• LogD (pH = 5.5): -14.309652
• LogD (pH = 7.4): -12.557682
• Log P: -7.4748745
• Molar Refractivity: 150.4536 cm^3
• Polarizability: 53.031017 Å^3
• Polar Surface Area: 334.59 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: crystalline

Safety Information

• RTECS: WK2236000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)
• Salt Data: 1.5 H2SO4
• Suitability: suitable for cell culture

DETAILS

Sigma Aldrich - D7253

Biochem/physiol Actions
Mode of action: inhibits bacterial protein synthesis at the level of the 30S ribosomal subunit and the 16S rRNA.
Application
Dihydrostreptomycin sesquisulfate is an antibiotic used in aminoglycoside uptake studies1,2. It has also been used as an electrode for a cochlear amplifier in the hair-cell bundle of lizards3.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - D5155

Application
Use to study bacterial protein synthesis, codon misreading, at the level of the 30S ribosomal subunit and the 16S rRNA.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information