(4S,4aS,6S,8aS)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-(dimethylamino)-3,8a-dihydroxy-1,8-dioxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxamide

• ChemBase ID: 171779
• Molecular Formular: C22H23ClN2O8
• Molecular Mass: 478.87962
• Monoisotopic Mass: 478.11429339
• SMILES: c1cc(c2c(c1O)C(=O)O[C@]2([C@@H]1CC(=O)[C@]2([C@@H](C1)[C@@H](C(=C(C2=O)C(=O)N)O)N(C)C)O)C)Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H](CC2=O)[C@]1(C)OC(=O)c2c1c(Cl)ccc2O)O)O)C
• InChI: InChI=1S/C22H23ClN2O8/c1-21(15-10(23)4-5-11(26)13(15)20(31)33-21)8-6-9-16(25(2)3)17(28)14(19(24)30)18(29)22(9,32)12(27)7-8/h4-5,8-9,16,26,28,32H,6-7H2,1-3H3,(H2,24,30)/t8-,9-,16-,21-,22-/m0/s1
• InChIKey: GFSLIMZISCAANG-AXVXPIMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,6S,8aS)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-(dimethylamino)-3,8a-dihydroxy-1,8-dioxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxamide
• IUPAC Traditional name: (4S,4aS,6S,8aS)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-2-benzofuran-1-yl]-4-(dimethylamino)-3,8a-dihydroxy-1,8-dioxo-4a,5,6,7-tetrahydro-4H-naphthalene-2-carboxamide
• Synonyms: (4S,4aS,6S,8aS)-6-[(1S)-7-Chloro-1,3-dihydro-4-hydroxy-1-methyl-3-oxo-1-isobenzofuranyl]-4-(dimethylamino)-1,4,4a,5,6,7,8,8a-octahydro-3,8a-dihydroxy-1,8-dioxo-2-naphthalenecarboxamide; Isoaureomycin; 7-Chloroisotetracycline; Isochlortetracycline

Database IDs

• CAS Number: 514-53-4
• PubChem SID: 164227689
• PubChem CID: 54678405

CALCULATED PROPERTIES

• Acid pKa: -2.5779622
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.4321619
• LogD (pH = 7.4): -1.473376
• Log P: -1.431897
• Molar Refractivity: 116.6831 cm^3
• Polarizability: 44.922546 Å^3
• Polar Surface Area: 167.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 202-205°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - I790000

An inactive metabolite of Chlortetracycline (CTC).

REFERENCES

• Collett, J., et al.: J. Pharm. Pharmacol., 22, 672 (1970)
• Zurhelle, G., et al.: J. Agric. Food Chem., 48, 6392 (1970)
• Diana, J., et al.: J. Pharm. Biomed. Anal., 39, 523 (1970)