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

• ChemBase ID: 72801
• Molecular Formular: C22H24N2O9
• Molecular Mass: 460.43396
• Monoisotopic Mass: 460.14818036
• SMILES: C1(=C([C@H]([C@H]2[C@@](C1=O)(C(=O)C1=C(c3c([C@]([C@H]1[C@@H]2O)(O)C)cccc3O)O)O)N(C)C)O)C(=O)N
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C
• InChI: InChI=1S/C22H24N2O9/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/h4-6,12-14,17,25-28,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
• InChIKey: JLGOGFIHBRJQHY-PXOLEDIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Synonyms: Terramycin; Liquamycin; Oxytetracycline

Database IDs

• CAS Number: 79-57-2
• PubChem SID: 162037722
• PubChem CID: 54675779

CALCULATED PROPERTIES

• Acid pKa: 0.2717006
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -4.791391
• LogD (pH = 7.4): -5.624763
• Log P: -4.764702
• Molar Refractivity: 115.3049 cm^3
• Polarizability: 43.96009 Å^3
• Polar Surface Area: 201.85 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1773

Research Area: Infection
Biological Activity:
Oxytetracycline(Terramycin) was the second of the broad-spectrum tetracycline group of antibiotics to be discovered. Oxytetracycline works by interfering with the ability of bacteria to produce proteins that are essential to them. Without these proteins the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection and the remaining bacteria are killed by the immune system or eventually die. Oxytetracycline is a broad spectrum antibiotic that is active against a wide variety of bacteria. Oxytetracycline is still used to treat infections caused by chlamydia (e.g. the chest infection psittacosis, the eye infection trachoma, and the genital infection urethritis) and infections caused by mycoplasma organisms. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Oxytetracycline