(4R,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 176149
• Molecular Formular: C22H24N2O9
• Molecular Mass: 460.43396
• Monoisotopic Mass: 460.14818036
• SMILES: c1cc(c2c(c1)[C@]([C@@H]1C(=C([C@]3([C@@H]([C@H]1O)[C@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)(O)C)O
• Canonical SMILES: CN([C@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C
• InChI: InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14-,17+,21-,22+/m1/s1
• InChIKey: IWVCMVBTMGNXQD-DVJPNYBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4R,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Synonyms: [4R-(4α,4aβ,5β,5aβ,6α,12aβ]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide; Hydroxy Quatrimycin; 4-epi-Oxytetracycline

Database IDs

• CAS Number: 14206-58-7
• PubChem SID: 164232059
• PubChem CID: 54678403

CALCULATED PROPERTIES

• Acid pKa: 0.24295226
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.5841894
• LogD (pH = 7.4): -7.485068
• Log P: -4.5983834
• Molar Refractivity: 115.3982 cm^3
• Polarizability: 43.880726 Å^3
• Polar Surface Area: 201.85 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pale Yellow Solid
• Melting Point: 184-186°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - O877505

A metabolite of Oxytetracycline (OTC); also a Tetracycline analogue as inhibitor of amyloid fibrils.

REFERENCES

• Eisner, H., et al.: J. Pharm. Exp. Ther., 142, 122 (1963)
• Nelis, H., et al.: Drug Metab. Dispos., 10, 142 (1963)
• Boecker, R., et al.: Drugs Exp. Clin. Res., 9, 813 (1963)