(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy]-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

• ChemBase ID: 168175
• Molecular Formular: C36H65NO13
• Molecular Mass: 719.9002
• Monoisotopic Mass: 719.44559115
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](C(=O)[C@@H]([C@H]1O)C)C)(O)C)OC1C(C(CC(O1)C)N(C)C)O)C)OC1OC(C(C(C1)(O)C)O)C)C)CC)(O)C
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2OC(C)C(C(C2)(C)O)O)[C@H](C)[C@@H](OC2OC(C)CC(C2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
• InChI: InChI=1S/C36H65NO13/c1-13-24-36(10,45)29(40)19(4)26(38)17(2)15-35(9,44)31(50-33-27(39)23(37(11)12)14-18(3)46-33)20(5)28(21(6)32(42)48-24)49-25-16-34(8,43)30(41)22(7)47-25/h17-25,27-31,33,39-41,43-45H,13-16H2,1-12H3/t17-,18?,19+,20+,21-,22?,23?,24-,25?,27?,28+,29-,30?,31-,33?,34?,35-,36-/m1/s1
• InChIKey: MWFRKHPRXPSWNT-VACSZJCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy]-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy]-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• Synonyms: 3''-O-Demethyl Erythromycin; Erythromycin C

Database IDs

• CAS Number: 1675-02-1
• PubChem SID: 162262307
• PubChem CID: 71316418

CALCULATED PROPERTIES

• Acid pKa: 12.423108
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -0.8352264
• LogD (pH = 7.4): 0.93013793
• Log P: 1.9532623
• Molar Refractivity: 181.2859 cm^3
• Polarizability: 73.861595 Å^3
• Polar Surface Area: 204.91 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E649980

Erythromycin (E649950) impurity. A related substance in Erythromycin drug.

REFERENCES

• Wilhelm, J.M., et al.: Antimicrobial. Agents Chem., 236, 50 (1967)