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

• ChemBase ID: 167204
• Molecular Formular: C21H23N3O7
• Molecular Mass: 429.42322
• Monoisotopic Mass: 429.15360009
• SMILES: c1cc(c2c(c1N)C[C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H]1Cc3c(N)ccc(c3C(=O)C1=C2O)O)O)O)C
• InChI: InChI=1S/C21H23N3O7/c1-24(2)15-9-6-7-5-8-10(22)3-4-11(25)13(8)16(26)12(7)18(28)21(9,31)19(29)14(17(15)27)20(23)30/h3-4,7,9,15,25,27-28,31H,5-6,22H2,1-2H3,(H2,23,30)/t7-,9-,15-,21-/m0/s1
• InChIKey: UNWRIWATQPEZLL-UVPAEMEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-7-amino-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,5aR,12aS)-7-amino-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: [4S-(4α,4aα,5aα,12aα)]-7-Amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Dihydrochloride; 7-Amino-6-demethyl-6-deoxytetracycline Dihydrochloride; 7-Aminosancycline Dihydrochloride; 7-Didemethyl Minocycline Dihydrochloride (>85% by HPLC)

Database IDs

• CAS Number: 95940-02-6
• PubChem SID: 162261337
• PubChem CID: 54676743

CALCULATED PROPERTIES

• Molar Refractivity: 112.812 cm^3
• Polarizability: 41.804497 Å^3
• Polar Surface Area: 187.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false
• Acid pKa: -2.1778069
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.2839527
• LogD (pH = 7.4): -6.0613666
• Log P: -3.9871638

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light-Tan to Brown Solid
• Melting Point: >200°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D439651

An impurity of Minocycline.

REFERENCES

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