4-{4,5-dihydroxy-9-methyl-3-oxo-1H,3H-naphtho[2,3-c]furan-1-yl}-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohex-1-ene-1-carboxamide

• ChemBase ID: 160764
• Molecular Formular: C22H22N2O8
• Molecular Mass: 442.41868
• Monoisotopic Mass: 442.13761567
• SMILES: c12c(c(ccc1)O)c(c1c(c2C)C(OC1=O)C1C(C(=C(C(=O)C1O)C(=O)N)O)N(C)C)O
• Canonical SMILES: CN(C1C(=C(C(=O)N)C(=O)C(C1C1OC(=O)c2c1c(C)c1c(c2O)c(O)ccc1)O)O)C
• InChI: InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)20(32-22(12)31)13-15(24(2)3)17(27)14(21(23)30)19(29)18(13)28/h4-6,13,15,18,20,25-28H,1-3H3,(H2,23,30)
• InChIKey: DRKMHDAKULCOKQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4,5-dihydroxy-9-methyl-3-oxo-1H,3H-naphtho[2,3-c]furan-1-yl}-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohex-1-ene-1-carboxamide
• IUPAC Traditional name: 4-{4,5-dihydroxy-9-methyl-3-oxo-1H-naphtho[2,3-c]furan-1-yl}-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohex-1-ene-1-carboxamide
• Synonyms: β-Apoterramycin; β-Apo-oxytetracycline; 4-(1,3-Dihydro-4,5-dihydroxy-9-methyl-3-oxonaphtho[2,3-c]furan-1-yl)-3-(dimethylamino)-2,5-dihydroxy-6-oxo-1-cyclohexene-1-carboxamide; α-Apoterramycin; α-Apo-oxytetracycline

Database IDs

• CAS Number: 18751-99-0; 18695-01-7
• PubChem SID: 162254899
• PubChem CID: 54710410

CALCULATED PROPERTIES

• Acid pKa: -2.2347748
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.6460063
• LogD (pH = 7.4): -1.6813518
• Log P: -1.6458116
• Molar Refractivity: 113.3047 cm^3
• Polarizability: 44.22138 Å^3
• Polar Surface Area: 170.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brown Solid
• Melting Point: >180°C (dec.); 198-203°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A729036

Oxytetracycline metabolite (absolute stereochemistry unknown)

Toronto Research Chemicals - A729035

Oxytetracycline metabolite (absolute stereochemistry unknown)

REFERENCES

• Mackie, R., et al.: Animal Biotechnol., 17, 157 (2006)
• Smyrniotakis, C., et al.: J. Pharm. Biomed. Anal., 43, 506 (2006)
• Li, D., et al.: Env. Toxicol. Chem., 27, 80 (2006)
• Paemen, L., et al.: Biochem. Pharmacol., 52, 105 (1996)
• Lykkeberg, A., et al.: J. Pharm. Biomed. Anal., 34, 325 (1996)
• Li, D., et al.: Env. Toxicol. Chem., 27, 80 (1996)