4-(Dimethylamino)-3,5,6,10,12,12alpha-Hexahydroxy-6-Methyl-1,11-Dioxo-1,4,4A,5,5A,6,11,12alpha-Octahydro-2-Tetracenecarboxamide
[CAS# 14206-58-7]

Identification

• Classification: API >> Antibiotics >> Tetracycline
• Name: 4-(Dimethylamino)-3,5,6,10,12,12alpha-Hexahydroxy-6-Methyl-1,11-Dioxo-1,4,4A,5,5A,6,11,12alpha-Octahydro-2-Tetracenecarboxamide
• Synonyms: 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6S,12aS)-; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, [4S-(4α,4aα,5α,5aα,6β,12aα)]-; 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
• Molecular Formula: C₂₂H₂₄N₂O₉
• Molecular Weight: 460.43
• CAS Registry Number: 14206-58-7
• SMILES: CN(C)C1C(\O)=C(/C(=O)C2(O)C1C(O)C4\C(=C2\O)C(=O)c3c(O)cccc3C4(C)O)C(N)=O
• 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/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)
• InChIKey: IWVCMVBTMGNXQD-UHFFFAOYSA-N

Properties

• Density: 1.717g/cm³ (Cal.)
• Boiling point: 839.646°C at 760 mmHg (Cal.)
• Flash point: 461.601°C (Cal.)
• Refractive index: 1.762 (Cal.)

References

• (1): Gilles Klopman, Liliana R. Stefan and Roustem D. Saiakhov. ADME evaluation: 2. A computer model for the prediction of intestinal absorption in humans, Eur. J. Pharm. Sci. 2002, 17 (4-5), 253-263A total of 50 drugs and their %HIA (Human Intestinal Absorption) values taken from the table given in the paper. "Flucloxacillin" was retrieved as "Floxacillin" from ChemIDplus. "Azimilide" had to be drawn as structure was not available for download from ChemIDplus (though it was depicted there).
• (2): Igor V. Tetko, Vsevolod Yu. Tanchuk, Tamara N. Kasheva, and Alessandro E. P. Villa. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices, J. Chem. Inf. Comput. Sci., 2001, 41 (6), pp 1488–1493