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108321-42-2 molecular structure
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(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2S,3S,4S,5S)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-(1-hydroxyethyl)oxane-3,4-diol; bis(sulfuric acid)

ChemBase ID: 131635
Molecular Formular: C20H44N4O18S2
Molecular Mass: 692.70936
Monoisotopic Mass: 692.20920259
SMILES and InChIs

SMILES:
CC([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@H]1[C@H]([C@@H]([C@](CO1)(C)O)NC)O)N)N)N)O)O)O.OS(=O)(=O)O.OS(=O)(=O)O
Canonical SMILES:
OS(=O)(=O)O.OS(=O)(=O)O.CN[C@H]1[C@H](O)[C@@H](OC[C@@]1(C)O)O[C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@H](C(O)C)[C@H]([C@@H]([C@H]1N)O)O)N
InChI:
InChI=1S/C20H40N4O10.2H2O4S/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19;2*1-5(2,3)4/h6-19,24-30H,4-5,21-23H2,1-3H3;2*(H2,1,2,3,4)/t6?,7-,8+,9+,10+,11-,12-,13-,14+,15+,16-,17-,18+,19-,20+;;/m0../s1
InChIKey:
UHEPSJJJMTWUCP-NKCAIAFTSA-N

Cite this record

CBID:131635 http://www.chembase.cn/molecule-131635.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2S,3S,4S,5S)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-(1-hydroxyethyl)oxane-3,4-diol; bis(sulfuric acid)
IUPAC Traditional name
(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2S,3S,4S,5S)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-(1-hydroxyethyl)oxane-3,4-diol; bis(sulfuric acid)
Synonyms
G 418 disulfate salt
G 418 disulfate salt solution
Antibiotic G418
抗生物質G418
G 418 二硫酸盐
CAS Number
108321-42-2
MDL Number
MFCD00058314
PubChem SID
24890581
162225912
24895058
24895333
24895193
PubChem CID
16218858

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16218858 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.420779  H Acceptors 14 
H Donor 10  LogD (pH = 5.5) -16.208046 
LogD (pH = 7.4) -10.701025  Log P -5.3008466 
Molar Refractivity 114.0036 cm3 Polarizability 48.22068 Å3
Polar Surface Area 248.39 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL expand Show data source
H2O: soluble50 mg/mL (As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 8 days.) expand Show data source
Apperance
powder expand Show data source
white powder 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
German water hazard class
3 expand Show data source
Risk Statements
42/43 expand Show data source
Safety Statements
22-36/37-45 expand Show data source
23-36/37-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H317-H334 expand Show data source
GHS Precautionary statements
P261-P280-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Concentration
50 mg/mL in H2O expand Show data source
Grade
Biotechnology Performance Certified expand Show data source
Potency
≥450 μg per mg (dried basis) expand Show data source
Suitability
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for plant cell culture expand Show data source
Impurities
≤10% water expand Show data source
endotoxin, tested expand Show data source
Sterility
sterile-filtered expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C20H40N4O10 · 2H2SO4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A8601 external link
Biochem/physiol Actions
G 418 blocks polypeptide synthesis by interfering with ribosomal function and inhibiting protein elongation.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein elongation. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Used for selection of G418 resistant transformed cells in molecular biology applications.
Other Notes
Aminoglycoside antibiotic similar in structure to gentamicin, neomycin and kanamycin.
Application
G 418 is a Micromonospora-produced aminoglycoside antibiotic with activity against protozoa and helminths1. G 418 disulfate salt is used for selection and maintenance of prokaryotic and eukaryotic cells transfected with a iNOS promoter construct and neomycin resistance gene2.
G 418 is an aminoglycoside antibiotic similar in structure to gentamycin. It is normally toxic towards eukaryotic and prokaryotic cells, but is useful for selection of cells stably transfected with neomycin resistance gene (Neo). The optimal concentration for selection and maintenance must be determined for each cell line. For bacteria and algae, concentrations of 5 μg/ml or less are recommended. Animal cells may require up to 300-500 μg/ml.Typically, resistance is conferred by one of two dominant genes of bacterial origin, which can be expressed in eukaryotic cells. Cells that are multiplying will be affected sooner than those that are quiescent. Cells in log phase may require three to seven days for selection. In general, concentrations of approximately 400 μg/ml for selection and 200 μg/ml for maintenance are required for mammalian cells.
Sigma Aldrich - G1279 external link
Biochem/physiol Actions
G 418 blocks polypeptide synthesis by interfering with ribosomal function and inhibiting protein elongation.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein elongation. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Other Notes
Aminoglycoside antibiotic similar in structure to gentamicin, neomycin and kanamycin.
Application
G 418 is a Micromonospora-produced aminoglycoside antibiotic with activity against protozoa and helminths1. G 418 disulfate salt is used for selection and maintenance of prokaryotic and eukaryotic cells transfected with a iNOS promoter construct and neomycin resistance gene2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - G5013 external link
Biochem/physiol Actions
G 418 blocks polypeptide synthesis by interfering with ribosomal function and inhibiting protein elongation.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein elongation. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Caution
Stable at 37 °C for 8 days.
Other Notes
Aminoglycoside antibiotic similar in structure to gentamicin, neomycin and kanamycin.
Reconstitution
Aqueous solutions stored frozen at -20 to -70 °C should be stable for approximately six months.
Application
Blocks protein synthesis by interfering with ribosomal function. Not normally used as a standard antibiotic, but rather for selection and maintenance of prokaryotic and eukaryotic cells stably transfected with neomycin resistance genes. Resistance is conferred by one of two dominant genes of bacterial origin which can be expressed in eukaryotic cells. The resistance genes are APH (3′) II or aminoglycoside phosphotransferase 3′(II) and aminoglycoside phosphotranferase 3′ (I) or APH (3′) I. The following concentrations of active ingredient may be used as a guide for selection: mammalian cells (400 ug/ml), plants (10 ug/ml), yeasts (500 ug/ml), and dictyostelium (10 ug/ml). Cells have variable resistance and multiplying cells will be affected sooner than those that are not. Cells in log phase may require three to seven days for selection. Varying concentrations should be tested. Additionally, fibroblast contamination in mixed cultures may be suppressed by using 100 ug/ml of the active ingredient for 2 days.
G 418 is a Micromonospora-produced aminoglycoside antibiotic with activity against protozoa and helminths. G 418 disulfate salt is used for selection and maintenance of prokaryotic and eukaryotic cells transfected with a iNOS promoter construct and neomycin resistance gene.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - A1720 external link
Biochem/physiol Actions
G 418 blocks polypeptide synthesis by interfering with ribosomal function and inhibiting protein elongation.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein elongation. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein synthesis at the level of the 70S and 80S ribosomes. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Other Notes
Aminoglycoside antibiotic similar in structure to gentamicin, neomycin and kanamycin.
Application
G 418 is a Micromonospora-produced aminoglycoside antibiotic with activity against protozoa and helminths1. G 418 disulfate salt is used for selection and maintenance of prokaryotic and eukaryotic cells transfected with a iNOS promoter construct and neomycin resistance gene2.
G 418 is an aminoglycoside antibiotic similar in structure to gentamycin. It is normally toxic towards eukaryotic and prokaryotic cells, but is useful for selection of cells stably transfected with neomycin resistance gene (Neo). The optimal concentration for selection and maintenance must be determined for each cell line. For bacteria and algae, concentrations of 5 μg/ml or less are recommended. Animal cells may require up to 300-500 μg/ml. Typically, resistance is conferred by one of two dominant genes of bacterial origin, which can be expressed in eukaryotic cells. Cells that are multiplying will be affected sooner than those are quiescent. Cells in log phase may require three to seven days for selection. In general, concentrations of approximately 400 μg/ml for selection and 200 μg/ml for maintenance are required for mammalian cells.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - G8168 external link
Biochem/physiol Actions
Mode of Action: Blocks polypeptide synthesis and inhibits elongation in the selection and maintenance of eucaryotic cells stably transfected with neomycin resistance gene
Physical form
50 mg/mL in tissue culture grade water
Application
G 418 is an aminoglycoside antibiotic similar in structure to gentamycin. It is normally toxic towards eukaryotic and prokaryotic cells, but is useful for selection of cells stably transfected with neomycin resistance gene (Neo). The optimal concentration for selection and maintenance must be determined for each cell line. For bacteria and algae, concentrations of 5 μg/ml or less are recommended. Animal cells may require up to 300-500 μg/ml. Typically, resistance is conferred by one of two dominant genes of bacterial origin, which can be expressed in eukaryotic cells. Cells that are multiplying will be affected sooner than those are quiescent. Cells in log phase may require three to seven days for selection. In general, concentrations of approximately 400 μg/ml for selection and 200 μg/ml for maintenance are required for mammalian cells.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 48753 external link
Biochem/physiol Actions
G 418 blocks polypeptide synthesis by interfering with ribosomal function and inhibiting protein elongation.
Mode of Action: Blocks polypeptide synthesis by inhibiting protein elongation. For use in the selection and maintenance of eukaryotic cells stably transfected with neomycin resistance genes.
Other Notes
Aminoglycoside antibiotic similar in structure to gentamicin, neomycin and kanamycin.
Inhibitor of neural phospholipase D activity3
Application
G 418 is a Micromonospora-produced aminoglycoside antibiotic with activity against protozoa and helminths1. G 418 disulfate salt is used for selection and maintenance of prokaryotic and eukaryotic cells transfected with a iNOS promoter construct and neomycin resistance gene2.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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