(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrate

• ChemBase编号: 153449
• 分子式: C22H26N2O10
• 平均质量: 478.44924
• 单一同位素质量: 478.15874504
• SMILES: C[C@]1(c2cccc(c2C(=O)C2=C([C@]3([C@@H]([C@H]([C@H]12)O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)O)O.O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C.O
• InChI: InChI=1S/C22H24N2O9.H2O/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29;/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31);1H2/t12-,13-,14+,17+,21-,22+;/m1./s1
• InChIKey: IBZHEBHGZFICKS-IFLJXUKPSA-N

名称和登记号

名称

• IUPAC标准名: (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrate
• IUPAC传统名: oxytetracycline hydrate
• 别名: 土霉素 二水合物; Oxytetracycline dihydrate

登记号

• CAS号: 6153-64-6
• EC号: 201-212-8
• MDL号: MFCD00151234
• PubChem SID: 24898000; 162247588
• PubChem CID: 54682936

理论计算性质

• Acid pKa: 0.24295226
• 质子受体: 10
• 质子供体: 7
• LogD (pH = 5.5): -5.5841894
• LogD (pH = 7.4): -7.485068
• Log P: -4.5983834
• 摩尔折射率: 115.3982 cm^3
• 极化性: 43.880726 Å^3
• 极化表面积: 201.85 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: 1 M HCl: soluble0.1 M, clear (yellow to yellow-orange)
• 外观: yellow crystalline

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97%; ≥99% (TLC)
• 燃烧残渣: ≤1.0%
• 杂质: ≤0.001% Phosphorus (P); ≤0.1% Insoluble matter
• 痕量阳离子: Al: ≤0.001%; Ca: ≤0.2%; Cu: ≤0.0005%; Fe: ≤0.002%; K: ≤0.005%; Mg: ≤0.005%; Na: ≤0.01%; Pb: ≤0.001%; Zn: ≤0.0005%
• 痕量阴离子: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• 产品线: BioXtra
• Empirical Formula (Hill Notation): C22H24N2O9 · 2H2O

详细说明

Sigma Aldrich - O5750

Biochem/physiol Actions
Antibiotic produced by Streptomyces rimosus.Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Active efflux, ribosome protection, tetracycline inactivation.

Sigma Aldrich - O4636

Biochem/physiol Actions
Antibiotic produced by Streptomyces rimosus.Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Active efflux, ribosome protection, tetracycline inactivation.
Oxytetracycline inhibits translation, which results in cell death. It binds to the 30S ribosomal subunit and prevents the amino-acyl Trna from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic so it can easily pass through a cell membrane and passively diffuses through channels in the bacterial membrane.
Application
Oxytetracycline is a tetracycline analog isolated from the actinomycete Streptomyces rimosus. Oxytetracycline is an antibiotic indicated for treatment of infections caused by Gram positive and Gram negative microorganisms such as Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae. It is used in studies on the oxytetracycline-resistance gene (otrA). It is used for fluorescence measurements of hepatocytes1.