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

• ChemBase ID: 173487
• Molecular Formular: C39H71NO13
• Molecular Mass: 761.97994
• Monoisotopic Mass: 761.49254134
• SMILES: [C@]1([C@@H](CC)OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H](C(=O)[C@@H]([C@H]1O)C)C)(C)OC)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)(C)OC
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)OC)O)C)C)(C)OC
• InChI: InChI=1S/C39H71NO13/c1-16-27-39(10,48-15)32(43)22(4)29(41)20(2)18-38(9,47-14)34(53-36-30(42)26(40(11)12)17-21(3)49-36)23(5)31(24(6)35(45)51-27)52-28-19-37(8,46-13)33(44)25(7)50-28/h20-28,30-34,36,42-44H,16-19H2,1-15H3/t20-,21-,22+,23+,24-,25+,26+,27-,28+,30-,31+,32-,33+,34-,36+,37-,38-,39-/m1/s1
• InChIKey: ZABLXHVYLJLDOX-HIKKGGSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12-hydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7,13-dimethoxy-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)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12-hydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7,13-dimethoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• Synonyms: 6,12-Di-O-methylerythromycin; 6,12-Di-O-methylerythromycin A; Clarithromycin EP Impurity F; 12-O-Methyl Clarithromycin

Database IDs

• CAS Number: 128940-83-0
• PubChem SID: 164229397
• PubChem CID: 14589671

CALCULATED PROPERTIES

• Acid pKa: 12.580753
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 1.094153
• LogD (pH = 7.4): 2.8595185
• Log P: 3.8826418
• Molar Refractivity: 195.5395 cm^3
• Polarizability: 79.56376 Å^3
• Polar Surface Area: 171.91 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M294630

12-O-Methyl Clarithromycin is a methylated impurity of the semi-synthetic macrolide antibiotic Clarithromycin (C559750). 12-O-Methyl Clarithromycin was shown to inhibit uptake of Clarithromycin into the lung cells.

REFERENCES

• Chen, X. et al.: Zhong. Yao., 17, 32 (2008)
• Yoshida, H. et al.: Jap. J. Antibiot., 53, 615 (2008)
• Omura, S. et al.: Yakug. Zas., 112, 593 (2008)