(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-4,7,12,13-tetrahydroxy-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

• ChemBase ID: 165534
• Molecular Formular: C33H62N2O12
• Molecular Mass: 678.85158
• Monoisotopic Mass: 678.43027543
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](/C(=N\OCOCCOC)/[C@@H]([C@H]1O)C)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O)C)CC)(O)C
• Canonical SMILES: COCCOCO/N=C/1\[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C33H62N2O12/c1-12-24-33(8,41)28(38)20(4)25(34-44-17-43-14-13-42-11)18(2)16-32(7,40)29(21(5)26(36)22(6)30(39)46-24)47-31-27(37)23(35(9)10)15-19(3)45-31/h18-24,26-29,31,36-38,40-41H,12-17H2,1-11H3/b34-25+/t18-,19-,20+,21+,22-,23+,24-,26+,27-,28-,29-,31+,32-,33-/m1/s1
• InChIKey: BNZRPTCUAOMSSH-MDOVVVHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-4,7,12,13-tetrahydroxy-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-4,7,12,13-tetrahydroxy-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• Synonyms: (9E)-3-O-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)erythromycin9-[O-[(2-Methoxyethoxy)methyl]oxime]; Decladinoseroxithromycin; (9E)-3-O-De(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)erythromycin 9-[O-[(2-Methoxyethoxy)methyl]oxime]; Roxithromycin Impurity B; Decladinose Roxithromycin (Roxithromycin Impurity B)

Database IDs

• CAS Number: 214902-82-6
• PubChem SID: 162259667
• PubChem CID: 21579398

CALCULATED PROPERTIES

• Acid pKa: 12.569733
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -1.3393397
• LogD (pH = 7.4): 0.21582907
• Log P: 1.8995637
• Molar Refractivity: 172.4893 cm^3
• Polarizability: 69.78028 Å^3
• Polar Surface Area: 189.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 88-91°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D226800

Roxithromycin impurity B. The inactive metabolite (M1) of Roxithromycin.

REFERENCES

• Ferrero, J., et al.: Drug Metab. Dispos., 18, 441 (1990)
• Gase, C., et al.: J. Antibiot., 44, 313 (1990)
• Markham, A., et al.: Drugs, 48, 297 (1990)
• Jarukamjorn, K., et al.: J. Pharm. Pharmacol., 50, 515 (1990)