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1397-89-3 分子结构
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(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

ChemBase编号:153350
分子式:C47H73NO17
平均质量:924.07902
单一同位素质量:923.48784988
SMILES和InChIs

SMILES:
C[C@H]1/C=C/C=C\C=C\C=C\C=C\C=C\C=C[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O
Canonical SMILES:
O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](C=C/C=C/C=C/C=C/C=C/C=C\C=C\[C@@H]([C@H]([C@H]([C@H](OC(=O)C[C@@H](C1)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
InChI:
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
InChIKey:
APKFDSVGJQXUKY-KKGHZKTASA-N

引用这个纪录

CBID:153350 http://www.chembase.cn/molecule-153350.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
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
IUPAC传统名
amphotericin B
别名
两性霉素 B 来源于链霉菌 属
Fungizone
Amphotericin B from Streptomyces sp.
CAS号
1397-89-3
EC号
215-742-2
MDL号
MFCD00877763
Beilstein号
78342
PubChem SID
24890749
162247489
24890655
PubChem CID
71311649

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
PubChem 71311649 external link

理论计算性质

理论计算性质

JChem
Acid pKa 3.5797393  质子受体 17 
质子供体 12  LogD (pH = 5.5) -2.3028812 
LogD (pH = 7.4) -2.3064086  Log P -2.3001616 
摩尔折射率 244.6705 cm3 极化性 94.662575 Å3
极化表面积 319.61 Å2 可自由旋转的化学键
里宾斯基五规则 false 

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)
溶解度
DMF: 1 M HCl (3:1): soluble, clear to slightly hazy expand 查看数据来源
DMF: 1 M HCl (3:1): soluble50 mg/mL, clear to slightly turbid, orange to very deep red expand 查看数据来源
DMF: soluble2-4 mg/mL expand 查看数据来源
DMSO: soluble30-40 mg/mL expand 查看数据来源
H2O: insoluble expand 查看数据来源
H2O: slightly soluble expand 查看数据来源
外观
powder expand 查看数据来源
RTECS编号
BU2625000 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
纯度
~80% (HPLC) expand 查看数据来源
适用性
plant cell culture tested expand 查看数据来源
suitable for cell culture expand 查看数据来源
产品质量级别
PREMIUM expand 查看数据来源
产品线
BioReagent expand 查看数据来源
Empirical Formula (Hill Notation)
C47H73NO17 expand 查看数据来源

详细说明

详细说明

Sigma Aldrich Sigma Aldrich
Sigma Aldrich -  A6804 external link
Application
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Biochem/physiol Actions
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.
Amphotericin B Streptomyces sp. Is a polyene antifungal antibiotic that forms membrane channels.
Sigma Aldrich -  A2411 external link
Application
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Recommended for antifungal use in cell culture media at 2.5 mg/L. Stable at 37 °C for 3 days.
Biochem/physiol Actions
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich -  A4888 external link
Biochem/physiol Actions
Amphotericin B is a polyene antifungal antibiotic from Streptomyces. It has an affinity for sterols, primarily ergosterols, of fungal cell membranes. It forms channels in the membranes, causing small molecules to leak out which contributes to cell death. Antimicrobial spectrum: fungi and yeast.
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.
Application
Amphotericin B is used to study the affects of the influx of calcium on antifungal activity, 1 and to study the binding and kinetics of Amphotericin B to sterols in monolayers, aqueous solutions, and phospholipid bilayers 2,3. It is also commonly used in tissue culture as an antifungal supplement.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich -  10042 external link
Biochem/physiol Actions
Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast.

参考文献

参考文献

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专利

专利

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