N-[(2S,3R,4S,6R)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide

• ChemBase ID: 165788
• Molecular Formular: C38H67NO14
• Molecular Mass: 761.93688
• Monoisotopic Mass: 761.45615583
• 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)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)(O)C
• Canonical SMILES: O=CN([C@@H]1C[C@@H](C)O[C@H]([C@@H]1O)O[C@@H]1[C@@H](C)[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@@H](C)C(=O)O[C@H](CC)[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]1(C)OC)C)C)O)(C)O)C
• InChI: InChI=1S/C38H67NO14/c1-14-26-38(10,46)31(43)21(4)28(41)19(2)16-37(9,48-13)33(53-35-29(42)25(39(11)18-40)15-20(3)49-35)22(5)30(23(6)34(45)51-26)52-27-17-36(8,47-12)32(44)24(7)50-27/h18-27,29-33,35,42-44,46H,14-17H2,1-13H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
• InChIKey: MQUSOKRVLWZDKB-KCBOHYOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4S,6R)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide
• IUPAC Traditional name: N-[(2S,3R,4S,6R)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide
• Synonyms: N-Demethyl-N-formyl-6-O-methylerythromycin; 3"-N-Demethyl-3"-N-formylclarithromycin; Clarithromycin EP Impurity H; N-Demethyl-N-formyl Clarithromycin

Database IDs

• CAS Number: 127140-69-6
• PubChem SID: 162259921
• PubChem CID: 71315393

CALCULATED PROPERTIES

• Acid pKa: 12.450447
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 2.4177089
• LogD (pH = 7.4): 2.4177072
• Log P: 2.417711
• Molar Refractivity: 190.569 cm^3
• Polarizability: 77.41102 Å^3
• Polar Surface Area: 199.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D231135

N-Demethyl-N-formylclarithromycin is an impurity of the semi-synthetic macrolide antibiotic Clarithromycin (C559750).

REFERENCES

• Chen, X. et al.: Zhong. Yao., 17, 32 (2008)