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

• ChemBase ID: 171040
• Molecular Formular: C23H25N3O7
• Molecular Mass: 455.4605
• Monoisotopic Mass: 455.16925016
• SMILES: c1cc(c2c(c1N(C)C)cc1c(c2O)C(=O)[C@]2([C@@H](C1)[C@@H](C(=C(C2=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]1Cc1cc3c(ccc(c3c(c1C2=O)O)O)N(C)C)O)O)C
• InChI: InChI=1S/C23H25N3O7/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/h5-7,11,17,27-29,33H,8H2,1-4H3,(H2,24,32)/t11-,17-,23-/m0/s1
• InChIKey: GUNFOZREGBRAGY-RYNWUYHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,12aS)-4,7-bis(dimethylamino)-3,10,11,12a-tetrahydroxy-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,12aS)-4,7-bis(dimethylamino)-3,10,11,12a-tetrahydroxy-1,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide
• Synonyms: 4,7-Bis(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-1,12-dioxo-2-naphthacenecarboxamide; Δ5a-11-Hydroxy-12-oxo Minocycline

Database IDs

• PubChem SID: 164226950
• PubChem CID: 71749231

CALCULATED PROPERTIES

• Acid pKa: -2.3013825
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.0835273
• LogD (pH = 7.4): -1.8560698
• Log P: -1.8169559
• Molar Refractivity: 121.732 cm^3
• Polarizability: 46.56654 Å^3
• Polar Surface Area: 164.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948925

An impurity of Minocycline (M344800).

REFERENCES

• Sokoloski, T.D., et al.: J. Pharm. Sci., 66, 1159 (1977)
• Naidong, W., et al.: J. Pharm. Biomed. Anal., 13, 905 (1977)