(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 ID: 153449
• Molecular Formular: C22H26N2O10
• Molecular Mass: 478.44924
• Monoisotopic Mass: 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

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 hydrate
• IUPAC Traditional name: oxytetracycline hydrate
• Synonyms: Oxytetracycline dihydrate; 土霉素 二水合物

Database IDs

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

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

• Solubility: 1 M HCl: soluble0.1 M, clear (yellow to yellow-orange)
• Apperance: yellow crystalline

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97%; ≥99% (TLC)
• Ignition Residue: ≤1.0%
• Impurities: ≤0.001% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: 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%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C22H24N2O9 · 2H2O

DETAILS

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.