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1405-41-0 molecular structure
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(2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid

ChemBase ID: 130786
Molecular Formular: C60H125N15O25S
Molecular Mass: 1488.785
Monoisotopic Mass: 1487.86917558
SMILES and InChIs

SMILES:
C[C@H]([C@@H]1CC[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)N.C[C@H]([C@@H]1CC[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)NC.CC1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H](CC[C@H](O1)CN)N)N)N)O.OS(=O)(=O)O
Canonical SMILES:
OS(=O)(=O)O.CN[C@@H]1[C@@H](O)[C@H](OCC1(C)O)O[C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H](CC[C@H]1N)[C@H](N)C)N.CN[C@@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OCC([C@@H]([C@H]1O)NC)(C)O)N)N)C.NC[C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OCC([C@@H]([C@H]1O)NC)(C)O)N)N
InChI:
InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21?;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20?;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19?;/m110./s1
InChIKey:
RDEIXVOBVLKYNT-UTRRJPTHSA-N

Cite this record

CBID:130786 http://www.chembase.cn/molecule-130786.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
IUPAC Traditional name
(2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
Synonyms
Gentamicin sulfate from Micromonospora purpurea
Gentamicin sulfate salt
Gentamicin sulfate
Gentamicin solution
Garamycin
Gentiomycin C
Gentamicin sulfate salt
庆大霉素 硫酸酯 来源于紫红小单孢菌
庆大霉素 硫酸盐
庆大霉素 C
庆大霉素 硫酸盐
正泰霉素
庆大霉素 硫酸酯
庆大霉素 溶液
CAS Number
1405-41-0
EC Number
215-778-9
MDL Number
MFCD00270181
PubChem SID
162225064
PubChem CID
71308338

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.549178  H Acceptors 12 
H Donor LogD (pH = 5.5) -17.685123 
LogD (pH = 7.4) -11.792577  Log P -3.1371555 
Molar Refractivity 118.0207 cm3 Polarizability 49.566326 Å3
Polar Surface Area 199.73 Å2 Rotatable Bonds 19 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.1 g/mL, clear, very faintly yellow expand Show data source
H2O: soluble50 mg/mL (As a stock solution. Stock solutions should be stored at -20 °C.) expand Show data source
H2O: soluble50 mg/mL (As stock solution, store at -20°C. Stable at 37°C for 5 days.) expand Show data source
Apperance
liquid expand Show data source
powder expand Show data source
Optical Rotation
[α]20/D +110±8°, c = 1% in H2O expand Show data source
pH
4.0-5.5 (0.1 g/mL in H2O) expand Show data source
RTECS
LY2625000 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
2 expand Show data source
nwg 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
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Concentration
1 mg/mL in 1 mM EDTA expand Show data source
10 mg/mL in deionized water expand Show data source
50 mg/mL gentamicin expand Show data source
50 mg/mL gentamicin (deionized water) expand Show data source
50 mg/mL in deionized water expand Show data source
50 μg/mL in H2O ( is the recommended working concentration for eukaryotic cell culture) expand Show data source
Grade
Biotechnology Performance Certified expand Show data source
for cell biology expand Show data source
Hybri-Max™ expand Show data source
Potency
~600 μg Gentamicin per mg expand Show data source
≥590 μg Gentamicin base per mg expand Show data source
Suitability
in accordance for cell culture expand Show data source
meets EP, USP testing specifications expand Show data source
meets USP testing specifications expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for hybridoma expand Show data source
Impurities
≤10 EU/mL endotoxins (LAL test) expand Show data source
≤10% water expand Show data source
endotoxin, tested expand Show data source
Sterility
sterile-filtered expand Show data source
γ-irradiated expand Show data source
Shelf Life
2 yr at 2-8 °C ( for sterile filtered solutions.) expand Show data source
Quality Level
PREMIUM expand Show data source
Quality
Prepared in tissue culture grade water. expand Show data source
Mol. Weight
Mr 694-723 expand Show data source
Linear Formula
C19-21H39-43N5O7 · 2.5H2SO4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 48757 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Sigma Aldrich - G4793 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Sigma Aldrich - 48760 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Unit Definition
1 U corresponds to 1 μg of the USP gentamicin sulfate reference standard
Sigma Aldrich - G1272 external link
Application
Recommended for use in cell culture applications at 5 ml/L and used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
作用方式:通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱:革兰氏阴性菌、革兰氏阳性菌和支原体。
Caution
Stable at 37 °C for 5 days.
Other Notes
Formulated to contain 10 mg/ml gentamicin in deionized water.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - G6896 external link
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Sigma Aldrich - G1397 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology and cell culture applications. Recommended for use in cell culture applications at 1 ml/L.
Biochem/physiol Actions
作用方式:通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱:革兰氏阴性菌、革兰氏阳性菌和支原体。
Caution
Stable at 37°C for 5 days.
Other Notes
Formulated to contain 50 mg/ml gentamicin in deionized water.
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - G4918 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - G1264 external link
Application
Recommended for use in cell culture applications at 50 mg/L
Used as a selection agent (gentamicin-resistance gene) in cell culture and molecular biology applications. Recommended for use in cell culture applications at 50 mg/L
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic that inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin; particularly strains of Pseudomonas, Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 48755 external link
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Preparation Note
sterile filtered
Sigma Aldrich - G1522 external link
Biochem/physiol Actions
作用方式:通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱:革兰氏阴性菌、革兰氏阳性菌和支原体。
法律信息
Hybri-Max 商标 Sigma-Aldrich Co. LLC
Sigma Aldrich - G1914 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Sigma Aldrich - G3632 external link
Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Sigma Aldrich - G8648 external link
Application
建议以 10-15μg/ml 的量用于分子生物学应用。
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Reconstitution
直接用无菌水 (5-20mg/ml) 在样品瓶中制备储存液。储存液应储存在 -20°C 下。在 37°C 下可稳定 5 天。

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PATENTS

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