(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 hydrochloride

• ChemBase ID: 133341
• Molecular Formular: C22H25ClN2O9
• Molecular Mass: 496.8949
• Monoisotopic Mass: 496.12485807
• 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.Cl
• 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.Cl
• InChI: InChI=1S/C22H24N2O9.ClH/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);1H/t12-,13-,14+,17+,21-,22+;/m1./s1
• InChIKey: UBDNTYUBJLXUNN-IFLJXUKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 hydrochloride
• IUPAC Traditional name: oxytetracycline hydrochloride
• Synonyms: Oxytetracycline hydrochloride; 土霉素 盐酸盐

Database IDs

• CAS Number: 2058-46-0
• EC Number: 218-161-2
• MDL Number: MFCD00135815
• Beilstein Number: 3853107
• PubChem SID: 162227618; 24898027; 24870318
• PubChem CID: 54680782
• E Number: E703

CALCULATED PROPERTIES

• Acid pKa: 0.24295226
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.5841894
• LogD (pH = 7.4): -7.485068
• Log P: -4.5983834
• Molar Refractivity: 115.3982 cm^3
• Polarizability: 43.880726 Å^3
• Polar Surface Area: 201.85 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: yellow crystalline

Safety Information

• RTECS: QI8225000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 63
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361d
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: HCl
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C22H24N2O9 · HCl
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - O5875

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). Oxytetracycline hydrochloride is used to study phagosome-lysosome (P-L) fusion in P388D1 cells1 and antibiotic susceptibilities of Mycopasma bovis isolates2. Product O5875 is ≥95% (HPLC), crystalline.
Biochem/physiol Actions
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.

Sigma Aldrich - 46598

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC