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

• ChemBase ID: 168041
• Molecular Formular: C22H24N2O8
• Molecular Mass: 444.43456
• Monoisotopic Mass: 444.15326574
• SMILES: c1ccc(c2c1[C@H]([C@@H]1C(=C([C@]3([C@@H]([C@H]1O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)C)O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@@H]1[C@H](C)c3cccc(c3C(=O)C1=C2O)O)O)O)C
• InChI: InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10-,14-,15+,17+,22+/m1/s1
• InChIKey: JBIWCJUYHHGXTC-IPJAVASBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: (4R,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide; [4R-(4α,4aβ,5β,5aβ,6α,12aβ)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide; 4-Epi-6-epi DoxycyclineDiscontinued

Database IDs

• CAS Number: 97583-08-9
• PubChem SID: 162262173
• PubChem CID: 54685534

CALCULATED PROPERTIES

• Acid pKa: -2.235276
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.28254
• LogD (pH = 7.4): -6.187371
• Log P: -3.435637
• Molar Refractivity: 113.8919 cm^3
• Polarizability: 43.13817 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E585915

4-Epi-6-epi Doxycycline is an impurity of Doxycycline (D561500).

REFERENCES

• Naidong, W., et al.: J. Pharm. Biomed. Anal., 8, 891 (1990)
• Castellanos Gil, E., et al.: J. Chromatogr., 895, 43 (1990)
• Capote, R., et al.: J. Sep. Sci., 25, 399 (1990)