(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}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

• ChemBase ID: 166423
• Molecular Formular: C37H67NO13
• Molecular Mass: 733.92678
• Monoisotopic Mass: 733.46124121
• 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)NC)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)(O)C
• Canonical SMILES: 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]2C[C@@](C)(OC)[C@H]([C@H](O2)C)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
• InChI: InChI=1S/C37H67NO13/c1-14-25-37(10,44)30(41)20(4)27(39)18(2)16-36(9,46-13)32(51-34-28(40)24(38-11)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-35(8,45-12)31(42)23(7)48-26/h18-26,28-32,34,38,40-42,44H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: CIJTVUQEURKBDL-RWJQBGPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy}-7-methoxy-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)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• Synonyms: N-Demethyl-6-O-methylerythromycin; 3"-N-Demethylclarithromycin; N-(Desmethyl)clarithromycin; N-Demethylclarithromycin; N-Desmethyl Clarithromycin

Database IDs

• CAS Number: 101666-68-6
• PubChem SID: 162260556
• PubChem CID: 11072636

CALCULATED PROPERTIES

• Acid pKa: 12.463151
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.3221992
• LogD (pH = 7.4): 0.7411352
• Log P: 2.8564675
• Molar Refractivity: 185.4936 cm^3
• Polarizability: 75.83101 Å^3
• Polar Surface Area: 191.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; Ethanol; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 200-202°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291575

N-Desmethyl Clarithromycin is a metabolite of Clarithromycin (C559750).

REFERENCES

• Jenuwein, T., et al.: Science, 293, 1074 (2001)
• Somech, R., et al.: Cancer Treat. Rev., 30, 461 (2001)