(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 179701
• Molecular Formular: C23H27N3O7
• Molecular Mass: 457.47638
• Monoisotopic Mass: 457.18490022
• SMILES: [C@]12(C(=C3C(=O)c4c(c(ccc4O)N(C)C)C[C@H]3C[C@H]2[C@@H](C(=C(C1=O)C(=O)N)O)N(C)C)O)O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H]1Cc3c(C(=O)C1=C2O)c(O)ccc3N(C)C)O)O)C
• InChI: InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
• InChIKey: DYKFCLLONBREIL-KVUCHLLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• Synonyms: Minomycin; Minocin; Minoderm; Arestin; Akamin; Aknemin; Solodyn; Dynacin; Sebomin; Mino-Tabs; Minocycline

Database IDs

• CAS Number: 10118-90-8
• PubChem SID: 164235611
• PubChem CID: 54675783

CALCULATED PROPERTIES

• Acid pKa: -2.2551746
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.4607291
• LogD (pH = 7.4): -5.0696445
• Log P: -3.3341916
• Molar Refractivity: 122.5402 cm^3
• Polarizability: 45.459297 Å^3
• Polar Surface Area: 164.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitory effect on 5-lipoxygenase,; inhibits apoptosis via attenuation of TNF-alpha

Product Information

• Application(s): Effective against tetracycline resistant Staphylococci in mice

REFERENCES

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• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6867
• Curtis, R.D. et al., Can. J. Chem., 1991, 69, 834, (N-15 nmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 182
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MQW100; MQW250