(1R,3S,5R,7R,8Z,12R,14Z,16Z,18Z,20Z,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

• ChemBase编号: 134056
• 分子式: C33H47NO13
• 平均质量: 665.72518
• 单一同位素质量: 665.30474057
• SMILES: C[C@@H]1C/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]2[C@H](O2)/C=C\C(=O)O1)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: C[C@@H]1C/C=C\C=C/C=C\C=C/[C@H](O[C@@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)N)O)C[C@@H]2O[C@@](C[C@H](C[C@@H]3[C@@H](/C=C\C(=O)O1)O3)O)(O)C[C@@H]([C@H]2C(=O)O)O
• InChI: InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3-,7-5-,8-6-,11-9-,13-12-/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
• InChIKey: NCXMLFZGDNKEPB-UDMGDOCSSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3S,5R,7R,8Z,12R,14Z,16Z,18Z,20Z,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0^5,^7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• IUPAC传统名: (1R,3S,5R,7R,8Z,12R,14Z,16Z,18Z,20Z,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0^5,^7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• 别名: 那他霉素; 游霉素; 那他霉素 制备; 游霉素 制备; Pimaricin; Pimaricin preparation

登记号

• CAS号: 7681-93-8
• EC号: 231-683-5
• MDL号: MFCD00135085
• Beilstein号: 1614878
• PubChem SID: 24898105; 162228333; 24899055
• PubChem CID: 71308755

理论计算性质

• Acid pKa: 3.5797393
• 质子受体: 13
• 质子供体: 7
• LogD (pH = 5.5): -1.6976327
• LogD (pH = 7.4): -1.70116
• Log P: -1.6949131
• 摩尔折射率: 169.8826 cm^3
• 极化性: 66.246475 Å^3
• 极化表面积: 230.99 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: aqueous suspension
• 密度: 1.0 g/mL at 20 °C(lit.)

安全信息

• RTECS编号: TK3325000
• 德国WGK号: 2; 3
• 个人保护装置: Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 浓度: ~2.5%
• 生物来源: from Streptomyces chattanoogensis
• 无菌消毒: γ-irradiated
• 产品质量级别: PREMIUM

详细说明

Sigma Aldrich - P0440

Biochem/physiol Actions
An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane.3
Application
Pimaricin is an amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. It is used to study pimaricin biosynthesis1 and as a fungicide in agar media2.

Sigma Aldrich - P9703

Biochem/physiol Actions
与麦角固醇特异性结合并阻止真菌生长的抗真菌多烯大环内脂。但不同于制霉菌素和菲律宾菌素不同，那他霉素不会改变细胞质膜的渗透性3
Application
Pimaricin is an amphoteric macrolide antifungal antibiotic from Streptomyces chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as a ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. Pimaricin is used as a fungicide in agar media. It is used to study the pleitropic regulator AdpAch 1 and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis2.