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

• ChemBase ID: 176147
• Molecular Formular: C23H25NO9
• Molecular Mass: 459.4459
• Monoisotopic Mass: 459.15293139
• 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)C(C)C)O)O)C2=O)(O)C)O
• Canonical SMILES: CC([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/C23H25NO9/c1-7(2)10-15-18(28)14-12(17(27)11-8(22(14,3)32)5-4-6-9(11)25)19(29)23(15,33)20(30)13(16(10)26)21(24)31/h4-7,10,14-15,18,25-26,28-29,32-33H,1-3H3,(H2,24,31)/t10-,14+,15+,18-,22+,23-/m0/s1
• InChIKey: ZAGCXKREUWQDIN-WNONJBPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5R,5aR,6S,12aS)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4-(propan-2-yl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aR,5R,5aR,6S,12aS)-3,5,6,10,12,12a-hexahydroxy-4-isopropyl-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Synonyms: [4S-(4α,4aα,5α,5aα,6β,12aα]-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 Hydrochloride; Berkmycen; Biostat; Geomycin; Hydroxytetracycline; Oxycline; Terramycin; Oxytetracycline HydrochlorideDISCONTINUED. See O877501

Database IDs

• CAS Number: 2058-46-0
• PubChem SID: 164232057
• PubChem CID: 54739049

CALCULATED PROPERTIES

• Acid pKa: -0.21957278
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -4.3123183
• LogD (pH = 7.4): -6.8687706
• Log P: -0.6587109
• Molar Refractivity: 116.2919 cm^3
• Polarizability: 44.17589 Å^3
• Polar Surface Area: 198.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Light Yellow Solid
• Melting Point: >178°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O877500

Antibiotic substance isolated from the elaboration products of the actinomycete, Streptomyces rimosus, grown on a suitable medium. Antibacterial.

REFERENCES

• Finlay, et al.: Science, 111, 85 (1950)
• Weiss, et al.: Antibiot. Chemother., 7, 374 (1950)
• Kruse, H., et al.: Microb. Drug. Resist., 5, 135, (1950)
• van den Bogaard, A., et al.: J. Antimicrob. Chemother., 45, 663 (1950)
• Nwosu, V., et al.: Res. Microbio