(1R,3S,5R,7R,12R,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: 156224
• 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)/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
• InChIKey: NCXMLFZGDNKEPB-YWDKRKKXSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3S,5R,7R,12R,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,12R,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 制备; 游霉素 制备; 游霉素; 那他霉素; 那他霉素; Natamycin preparation; Pimaricin preparation; Natamycin; Pimaricin; Natamycin

登记号

• CAS号: 7681-93-8
• EC号: 231-683-5
• MDL号: MFCD00135085
• Beilstein号: 1614878
• PubChem SID: 162250362; 24887548
• PubChem CID: 57417192
• E编码: E235

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

• 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
• 保存温度: 2-8°C

产品相关信息

• 纯度: ~90% (N)
• 级别: VETRANAL™, analytical standard
• 品质说明: aqueous suspension 2.5%; sterile
• Empirical Formula (Hill Notation): C33H47NO13

详细说明

Sigma Aldrich - 80482

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.1
Other Notes
Polyene antibiotic, review2

Sigma Aldrich - 32417

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1
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC