(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: 168011
• Molecular Formular: C23H27N3O7
• Molecular Mass: 457.47638
• Monoisotopic Mass: 457.18490022
• SMILES: c1cc(c2c(c1N(C)C)C[C@@H]1C(=C([C@]3([C@@H](C1)C(C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)O
• Canonical SMILES: CN(C1C(=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-JCNZWBQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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: (4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: [4R-(4α,4aβ,5aβ,12aβ)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydro-1,11-dioxo-2-naphthacenecarboxamide; Epiminocycline; 4-Epi Minocycline (>80%, contains unidentified salts)

Database IDs

• CAS Number: 43168-51-0
• PubChem SID: 162262143
• PubChem CID: 54697989

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

Physical Property

• Solubility: Acetone (sparingly); DMSO; Ethanol (sparingly); Methanol (sparingly)
• Apperance: Yellow Orange Solid
• Melting Point: >196°C (dec)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E588540

An impurity of Minocycline.

REFERENCES

• Naidong, W., et al.: J. Pharm. Biomed. Anal., 13, 905 (1995)