CAS 1405-41-0|Gentamicin solution|庆大霉素硫酸盐|(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)ox...

基本信息

化学结构

分子式

C₆₀H₁₂₅N₁₅O₂₅S

分子量

1488.785

精确质量

1487.86917558

电荷

0

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

Canonic 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

Isomeric 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

计算属性

JChem

Acid pKa

12.549178

质子受体

12

质子供体

8

LogD (pH = 5.5)

-17.685123

LogD (pH = 7.4)

-11.792577

Log P

-3.1371555

摩尔折射率

118.0207

极化性

49.566326

极化表面积

199.73

可自由旋转的化学键

19

里宾斯基五规则

false

数据来源

产品目录

学术数据

数据来源

名称和标识

别名

Gentamicin solution庆大霉素硫酸盐庆大霉素 C正泰霉素Gentamicin sulfate salt庆大霉素溶液庆大霉素硫酸酯庆大霉素硫酸盐Gentamicin sulfateGaramycinGentamicin sulfate from Micromonospora purpurea庆大霉素硫酸酯来源于紫红小单孢菌Gentiomycin CGentamicin sulfate salt

IUPAC传统名

(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标准名

(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

名称和标识

数据登录号

MDL号

EC号

CAS号

PubChem SID

PubChem CID

数据登录号

化合物性质

理化性质

外观

powder

liquid

溶解度

H2O: soluble50 mg/mL (As a stock solution. Stock solutions should be stored at -20 °C.)

H2O: soluble50 mg/mL (As stock solution, store at -20°C. Stable at 37°C for 5 days.)

H2O: soluble0.1 g/mL, clear, very faintly yellow

pH值

4.0-5.5 (0.1 g/mL in H2O)

[α]20/D +110±8°, c = 1% in H2O

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

Sigma Aldrich

G3632

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

G8648

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。

G1914

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

G1522

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

G6896

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.

G1264

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

G1272

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

G1397

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

G4793

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.

G4918

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

48760

Application
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。
Unit Definition
1U 对应于 1μg USP 级硫酸庆大霉素标准品

48757

Application
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。

48755

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。
Preparation Note
无菌过滤

描述信息

参考文献

PubChem文献

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生物活性

PubChem BioAssay

生物活性

化合物信息

ID:130786