(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

• ChemBase编号: 155901
• 分子式: C42H69NO15
• 平均质量: 827.99496
• 单一同位素质量: 827.46672051
• SMILES: C[C@@H]1C/C=C\C=C\[C@@H]([C@@H](C[C@@H]([C@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C)O[C@H]1C[C@@]([C@H]([C@@H](O1)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)[C@@H](O)/C=C/C=C\C[C@H](OC(=O)C[C@H]([C@@H]([C@@H]1O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)N(C)C)O[C@@H]1O[C@@H](C)[C@@H]([C@](C1)(C)O)OC(=O)CC(C)C)OC)OC(=O)C)C
• InChI: InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
• InChIKey: XJSFLOJWULLJQS-XRUKWLHHSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
• IUPAC传统名: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
• 别名: Josamycin; Josamycin solution

登记号

• CAS号: 16846-24-5
• EC号: 231-791-2; 240-871-6
• MDL号: MFCD00211043
• PubChem SID: 162250039; 24881768
• PubChem CID: 71312234

理论计算性质

• Acid pKa: 12.6682625
• 质子受体: 13
• 质子供体: 3
• LogD (pH = 5.5): 0.852045
• LogD (pH = 7.4): 2.6009817
• Log P: 3.216376
• 摩尔折射率: 211.0335 cm^3
• 极化性: 84.798904 Å^3
• 极化表面积: 206.05 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 2; nwg
• 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: ≥98.0% (UV)
• 浓度: 1 mg/mL in 1 mM EDTA
• Empirical Formula (Hill Notation): C42H69NO15

详细说明

Sigma Aldrich - 59983

Application
Josamycin is used to study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.
Josamycin is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics, immunomodulatory effects , the suppression of matrix metalloproteinase production as well as study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.
Biochem/physiol Actions
Josamycin inhibits bacterial protein biosynthesis by inhibiting peptidyltransferase and ribosomal translocation, and depleting the intracellular pools of aminoacyl-tRNAs available for protein synthesis by drop-off and incomplete peptidyl-tRNA hydrolase activity. 1. Josamycin slows down formation of the first peptide bond of a nascent peptide in an amino acid-dependent way and inhibits formation of the second or third peptide bond 2.