(4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; sulfuric acid

• ChemBase ID: 175420
• Molecular Formular: C21H23N3O13S
• Molecular Mass: 557.48462
• Monoisotopic Mass: 557.09515881
• SMILES: c1c(c(c2c(c1)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)[N+](=O)[O-].S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H]1Cc3ccc(c(c3C(=O)C1=C2O)O)[N+](=O)[O-])O)O)C
• InChI: InChI=1S/C21H21N3O9.H2O4S/c1-23(2)14-9-6-8-5-7-3-4-10(24(32)33)15(25)11(7)16(26)12(8)18(28)21(9,31)19(29)13(17(14)27)20(22)30;1-5(2,3)4/h3-4,8-9,14,25,27-28,31H,5-6H2,1-2H3,(H2,22,30);(H2,1,2,3,4)/t8-,9-,14-,21-;/m0./s1
• InChIKey: NUWRJZJADQYDTA-JYXIAGFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; sulfuric acid
• IUPAC Traditional name: (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide; sulfuric acid
• Synonyms: 9-Nitro-6-demethyl-6-deoxytetracycline Sulfate; [4S-(4α,4aα,5aα,12aα)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxamide Sulfate; 9-Nitrosancycline Monosulfate

Database IDs

• CAS Number: 2791-13-1
• PubChem SID: 164231330
• PubChem CID: 71751113

CALCULATED PROPERTIES

• Acid pKa: -2.395944
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.8685896
• LogD (pH = 7.4): -5.9818697
• Log P: -2.74447
• Molar Refractivity: 115.4363 cm^3
• Polarizability: 42.649677 Å^3
• Polar Surface Area: 207.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - N521005

Intermediate in the preparation of active 9-Amino-tetracyclines.

REFERENCES

• Miller, G., et al.: J. Pharm. Sci., 66, 88 (1977)
• Nelson, M., et al.: J. Med. Chem., 37, 1355 (1977)