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3810-74-0(anhydrous) molecular structure
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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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)

ChemBase ID: 130846
Molecular Formular: C42H84N14O36S3
Molecular Mass: 1457.38356
Monoisotopic Mass: 1456.43347808
SMILES and InChIs

SMILES:
C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC)(C=O)O.C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC)(C=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=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-YZTFXSNBSA-N

Cite this record

CBID:130846 http://www.chembase.cn/molecule-130846.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
IUPAC Traditional name
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-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
Synonyms
Streptomycin solution
Streptomycin sulfate salt
Streptomycin sesquisulfate hydrate
Streptomycini sulfas
链霉素 溶液
链霉素 硫酸盐
链霉素倍半硫酸盐
硫酸链霉素
CAS Number
3810-74-0(anhydrous)
3810-74-0
EC Number
223-286-0
231-791-2
MDL Number
MFCD00037023
Beilstein Number
3894995
PubChem SID
24899525
24888475
24899445
24870421
24899705
24899470
24899828
162225124
PubChem CID
6419957

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
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 cm3 Polarizability 52.500404 Å3
Polar Surface Area 331.43 Å2 Rotatable Bonds 18 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.1 g/mL, clear expand Show data source
Apperance
powder expand Show data source
white to off-white powder expand Show data source
RTECS
WK4990000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
63-22 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
H302-H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
~95% (T) expand Show data source
Concentration
~1 mg/mL in 1 mM EDTA expand Show data source
Grade
analytical standard expand Show data source
Biotechnology Performance Certified expand Show data source
Ph Eur expand Show data source
VETRANAL™, analytical standard expand Show data source
Potency
≥720 I.U. per mg expand Show data source
≥720 I.U. per mg (dried basis) expand Show data source
Suitability
cell culture tested expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for mouse embryo cell culture expand Show data source
Impurities
endotoxin, tested expand Show data source
Sterility
γ-irradiated expand Show data source
Loss on Drying
≤5% loss on drying expand Show data source
Mol. Weight
calculated mol wt 1457.38 ((C21H39N7O12)2 ?3H2O4S) expand Show data source
Linear Formula
C21H39N7O12 · 1.5 H2SO4 expand Show data source
Empirical Formula (Hill Notation)
C21H39N7O12 · 1.5H2O4S · xH2O expand Show data source
C21H39N7O12 · 1.5H2SO4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - S0774 external link
Application
Used together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - S1277 external link
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Recommended for use in embryo culture at 50 mg/L. Stock solutions should be sterile-filtered and stored at 2-8 °C for up to a month or at -20 °C for extended periods. Solutions are stable at 37 °C for 3 days. Use to inhibit bacterial protein synthesis at the level of initiation. Use to study mechanisms of streptomycin resistance. Use together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.
Sigma Aldrich - S1567 external link
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Sigma Aldrich - S9137 external link
Application
建议以 100mg/L 的量用于细胞培养应用。储存液应经过无菌过滤,在 2-8°C 下保存最多一个月或在 -20°C 下长期保存。溶液在 37°C 下可稳定 3 天。
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 46754 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 85880 external link
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Inhibits initiation and causes misreading of mRNA in protein synthesis1; Removal of DNA in cloning and expression of avidin in E. coli2.
Sigma Aldrich - 85884 external link
Application
Used together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Sigma Aldrich - S2522 external link
Application
建议以 25-50μg/ml 的量用于分子生物学应用。
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Reconstitution
直接在样品瓶中用无菌水 (25-20mg/ml) 制备储存液。储存液应在 -20°C 下保存。在 37°C 下可稳定 3 天。
Sigma Aldrich - S6501 external link
Application
Used to inhibit bacterial protein synthesis at the level of initiation inhibition.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

REFERENCES

REFERENCES

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PATENTS

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