calcium bis((1S,4aS,11S,12S,12aR)-3-carbamoyl-1-(dimethylamino)-4a,5,7,11,12-pentahydroxy-11-methyl-4,6-dioxo-1,4,4a,6,11,11a,12,12a-octahydrotetracen-2-olate)

• ChemBase ID: 134224
• Molecular Formular: C44H46CaN4O18
• Molecular Mass: 958.93004
• Monoisotopic Mass: 958.24330163
• SMILES: C[C@]1(c2cccc(c2C(=O)C2=C([C@]3([C@@H]([C@H](C12)O)[C@@H](C(=C(C3=O)C(=O)N)[O-])N(C)C)O)O)O)O.C[C@]1(c2cccc(c2C(=O)C2=C([C@]3([C@@H]([C@H](C12)O)[C@@H](C(=C(C3=O)C(=O)N)[O-])N(C)C)O)O)O)O.[Ca+2]
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)C1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)[O-])C.CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)C1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)[O-])C.[Ca+2]
• InChI: InChI=1S/2C22H24N2O9.Ca/c2*1-21(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;/h2*4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31);/q;;+2/p-2/t2*12?,13-,14+,17+,21-,22+;/m11./s1
• InChIKey: KIPLYOUQVMMOHB-JOFVZRTQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium bis((1S,4aS,11S,12S,12aR)-3-carbamoyl-1-(dimethylamino)-4a,5,7,11,12-pentahydroxy-11-methyl-4,6-dioxo-1,4,4a,6,11,11a,12,12a-octahydrotetracen-2-olate)
• IUPAC Traditional name: calcium bis((1S,4aS,11S,12S,12aR)-3-carbamoyl-1-(dimethylamino)-4a,5,7,11,12-pentahydroxy-11-methyl-4,6-dioxo-1,11a,12,12a-tetrahydrotetracen-2-olate)
• Synonyms: Oxytetracycline hemicalcium salt; 土霉素 半钙盐

Database IDs

• CAS Number: 15251-48-6
• EC Number: 239-293-7
• MDL Number: MFCD00151362
• PubChem SID: 24897968; 162228501
• PubChem CID: 71308776

CALCULATED PROPERTIES

• Acid pKa: 0.24295226
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -5.5841894
• LogD (pH = 7.4): -7.485068
• Log P: -4.5983834
• Molar Refractivity: 125.9485 cm^3
• Polarizability: 43.595413 Å^3
• Polar Surface Area: 204.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - O2756

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.
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.