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

• ChemBase ID: 174723
• Molecular Formular: C22H25N3O7
• Molecular Mass: 443.4498
• Monoisotopic Mass: 443.16925016
• 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)NC
• Canonical SMILES: CNc1ccc2c(c1O)C(=O)C1=C(O)[C@]3([C@@H](C[C@@H]1C2)[C@H](N(C)C)C(=C(C3=O)C(=O)N)O)O
• InChI: InChI=1S/C22H25N3O7/c1-24-11-5-4-8-6-9-7-10-15(25(2)3)18(28)14(21(23)31)20(30)22(10,32)19(29)13(9)17(27)12(8)16(11)26/h4-5,9-10,15,24,26,28-29,32H,6-7H2,1-3H3,(H2,23,31)/t9-,10-,15-,22-/m0/s1
• InChIKey: KTQLKXJOFVMDMQ-REXXEDAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-9-(methylamino)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-9-(methylamino)-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: (4S,4aS,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-(methylamino)-1,11-dioxo-2-naphthacenecarboxamide; 9-Methylamino-6-deoxy-6-demethyltetracycline; 9-Monodemethyl MinocyclineDISCONTINUED

Database IDs

• CAS Number: 4769-39-5
• PubChem SID: 164230633
• PubChem CID: 54741668

CALCULATED PROPERTIES

• Acid pKa: -2.174822
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.091264
• LogD (pH = 7.4): -5.7151484
• Log P: -3.9500086
• Molar Refractivity: 118.3054 cm^3
• Polarizability: 43.632347 Å^3
• Polar Surface Area: 173.42 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M527005

A Tetracycline derivative for use in antibiotic pharmaceutical compositions.

REFERENCES

• Kisker, C., et al.: J. Mol. Biol., 247, 260 (1995)
• Brodersen, D., et al.: Cell, 103, 1143 (1995)
• Aleksandrov, A., et al.: ChemBioChem., 8, 675 (1995)
• Aleksandrov, A., et al.: J. Mol. Biol., 378, 896 (1995)