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

• ChemBase ID: 160326
• Molecular Formular: C23H28N4O6
• Molecular Mass: 456.49162
• Monoisotopic Mass: 456.20088464
• SMILES: c1cc(c2c(c1N(C)C)C[C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)N)C2=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=C2N)c(O)ccc3N(C)C)O)O)C
• InChI: InChI=1S/C23H28N4O6/c1-26(2)12-5-6-13(28)15-10(12)7-9-8-11-17(27(3)4)19(30)16(22(25)32)21(31)23(11,33)20(24)14(9)18(15)29/h5-6,9,11,17,28,30,33H,7-8,24H2,1-4H3,(H2,25,32)/t9-,11-,17-,23-/m0/s1
• InChIKey: MTKKGPNRTNKQIP-KVUCHLLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-12-amino-4,7-bis(dimethylamino)-3,10,12a-trihydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,5aR,12aS)-12-amino-4,7-bis(dimethylamino)-3,10,12a-trihydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: (4S,4aS,5aR,12aS)-12-Amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12a-trihydroxy-1,11-dioxo-2-naphthacenecarboxamide; 12-Amino Minocycline

Database IDs

• CAS Number: 864073-42-7
• PubChem SID: 162254461
• PubChem CID: 54681877

CALCULATED PROPERTIES

• Acid pKa: -2.194553
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.3034196
• LogD (pH = 7.4): -3.1917727
• Log P: -3.179357
• Molar Refractivity: 124.1977 cm^3
• Polarizability: 45.953175 Å^3
• Polar Surface Area: 170.42 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A618285

An impurity of Minocycline (M344800). Used in the preparation of calpain inhibitors.

REFERENCES

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