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25389-94-0 分子结构
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(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol

ChemBase编号:1043
分子式:C18H36N4O11
平均质量:484.49864
单一同位素质量:484.23805799
SMILES和InChIs

SMILES:
O([C@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CN)[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)N)N
Canonical SMILES:
OC[C@H]1O[C@H](O[C@H]2[C@H](N)C[C@@H]([C@H]([C@@H]2O)O[C@H]2O[C@H](CN)[C@H]([C@@H]([C@H]2O)O)O)N)[C@@H]([C@H]([C@@H]1O)N)O
InChI:
InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
InChIKey:
SBUJHOSQTJFQJX-NOAMYHISSA-N

引用这个纪录

CBID:1043 http://www.chembase.cn/molecule-1043.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
IUPAC传统名
kanamycin
商标名
Bekanamycin
Kanamycin A
Kanamycin B
Kenamycin A
Klebcil
别名
KAN
Aminodeoxykanamycin
Kanamycin Base
Kanamycin Sulfate
Nebramycin Factor 5
Kanamycin
Kanamycin solution from Streptomyces kanamyceticus
CAS号
25389-94-0
8063-07-8
MDL号
MFCD00070289
PubChem SID
160964506
46508178
PubChem CID
6032

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
Sigma Aldrich
K0129 external link 加入购物车 请登录
K0254 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.109839  质子受体 15 
质子供体 11  LogD (pH = 5.5) -18.059649 
LogD (pH = 7.4) -12.666778  Log P -7.0609136 
摩尔折射率 106.1345 cm3 极化性 45.27121 Å3
极化表面积 282.61 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -3.1  LOG S -0.72 
溶解度 9.23e+01 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
外观
liquid expand 查看数据来源
疏水性(logP)
-6.3 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
德国WGK号
2 expand 查看数据来源
危险公开号
61 expand 查看数据来源
安全公开号
53-45 expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H360 expand 查看数据来源
GHS警示性声明
P201-P308 + P313 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
浓度
10 mg/mL in 0.9% NaCl expand 查看数据来源
50 mg/mL in 0.9% NaCl expand 查看数据来源
适用性
suitable for cell culture expand 查看数据来源
杂质
endotoxin, tested expand 查看数据来源
无菌消毒
sterile-filtered expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank -  DB01172 external link
Item Information
Drug Groups approved
Description Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components. [PubChem]
Indication For treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.
Pharmacology Kanamycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Toxicity Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance.
Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Kanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.
Half Life 2.5 hours
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  K0129 external link
Application
Recommended for use in cell culture applications at 10 ml/L.
Biochem/physiol Actions
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Caution
Stable at 37°C for 5 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich -  K0254 external link
Application
Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene. Recommended for use in cell culture applications at 2 ml/L.
Biochem/physiol Actions
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Caution
Stable at 37 °C for 5 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

参考文献

参考文献

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专利

专利

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