bis(1-[(1S,2R,3R,4S,5R,6R)-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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)

• ChemBase ID: 73265
• Molecular Formular: C42H84N14O36S3
• Molecular Mass: 1457.38356
• Monoisotopic Mass: 1456.43347808
• SMILES: S(=O)(=O)(O)O.S(=O)(=O)(O)O.S(=O)(=O)(O)O.[C@H]1([C@H]([C@@H]([C@H]([C@@H]([C@H]1NC(=N)N)O)NC(=N)N)O[C@H]1[C@H](O[C@@H]2O[C@H]([C@@H]([C@H]([C@@H]2NC)O)O)CO)[C@@]([C@@H](O1)C)(O)C=O)O)O.[C@H]1([C@H]([C@@H]([C@H]([C@@H]([C@H]1NC(=N)N)O)NC(=N)N)O[C@H]1[C@H](O[C@@H]2O[C@H]([C@@H]([C@H]([C@@H]2NC)O)O)CO)[C@@]([C@@H](O1)C)(O)C=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)C=O)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)C=O)C)[C@H]([C@@H]([C@H]1O)O)NC
• InChI: InChI=1S/2C21H39N7O12.3H2O4S/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*4-18,26,29,31-36H,3H2,1-2H3,(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: QTENRWWVYAAPBI-YCRXJPFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(1-[(1S,2R,3R,4S,5R,6R)-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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• IUPAC Traditional name: bis(1-[(1S,2R,3R,4S,5R,6R)-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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• Synonyms: Streptomycin sulfate

Database IDs

• CAS Number: 3810-74-0
• PubChem SID: 162038185
• PubChem CID: 19648

CALCULATED PROPERTIES

• Acid pKa: 10.877018
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -13.912841
• LogD (pH = 7.4): -12.161263
• Log P: -7.651423
• Molar Refractivity: 149.4707 cm^3
• Polarizability: 52.500404 Å^3
• Polar Surface Area: 331.43 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: sulfate

DETAILS

Selleck Chemicals - S2572

Research Area: Infection
Biological Activity:
Streptomycin sulfate is a sulfate salt of streptomycin that is a protein synthesis inhibitor. Streptomycin is an antibiotic drug, the first of a class of drugs called aminoglycosides to be discovered, and was the first antibiotic remedy for tuberculosis. Streptomycin is derived from the actinobacterium Streptomyces griseus. Streptomycin is a bactericidal antibiotic. Streptomycin binds to the S12 Protein of the 30S subunit of the bacterial ribosome, interfering with the binding of formyl-methionyl-tRNA to the 30S subunit. This prevents initiation of protein synthesis and leads to death of microbial cells. Humans have structurally different ribosomes from bacteria, thereby allowing the selectivity of this antibiotic for bacteria. However at low concentrations Streptomycin only inhibits growth of the bacteria by inducing prokaryotic ribosomes to misread mRNA. Streptomycin inhibits both Gram-positive and Gram-negative bacteria, and is a useful broad spectrum antibiotic. [1][2]References on Streptomycin sulfate[1] http://en.wikipedia.org/wiki/Streptomycin, , [2] J Mol Biol., 2007 Dec 7, 374(4):1065-76

REFERENCES

• Sharma D et al. J Mol Biol. 2007 Dec 7; 374(4):1065-76.