(2R,3S,4S,5R,8R,10E,12S,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-12,13-dihydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-methoxy-2,4,6,8,10,12-hexamethyl-9-oxopentadec-10-enoic acid

• ChemBase ID: 160650
• Molecular Formular: C38H69NO13
• Molecular Mass: 747.95336
• Monoisotopic Mass: 747.47689127
• SMILES: [C@]([C@@H](CC)O)(/C=C(/C(=O)[C@@H](CC([C@@H]([C@H]([C@@H]([C@H](C(=O)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)(C)OC)C)\C)(O)C
• Canonical SMILES: CC[C@H]([C@](/C=C(/C(=O)[C@@H](CC([C@@H]([C@H]([C@@H]([C@H](C(=O)O)C)O[C@@H]1O[C@H](C)[C@@H]([C@](C1)(C)OC)O)C)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)N(C)C)(OC)C)C)\C)(O)C)O
• InChI: InChI=1S/C38H69NO13/c1-15-27(40)36(8,46)17-20(2)29(41)21(3)18-38(10,48-14)33(52-35-30(42)26(39(11)12)16-22(4)49-35)23(5)31(24(6)34(44)45)51-28-19-37(9,47-13)32(43)25(7)50-28/h17,21-28,30-33,35,40,42-43,46H,15-16,18-19H2,1-14H3,(H,44,45)/b20-17+/t21-,22-,23+,24-,25+,26+,27-,28+,30-,31+,32+,33-,35+,36+,37-,38?/m1/s1
• InChIKey: QHQCTXVXTRAEAT-YKMSDKBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,8R,10E,12S,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-12,13-dihydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-methoxy-2,4,6,8,10,12-hexamethyl-9-oxopentadec-10-enoic acid
• IUPAC Traditional name: (2R,3S,4S,5R,8R,10E,12S,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-12,13-dihydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-methoxy-2,4,6,8,10,12-hexamethyl-9-oxopentadec-10-enoic acid
• Synonyms: seco 10,11-Didehydro-11-deoxy-6-O-methylerythromycin; seco 10,11-Didehydro-11-deoxy-clarithromycin; 3-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-12,13-dihydroxy-6-methoxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-10-pentadecenoic Acid; seco 10,11-Anhydro Clarithromycin

Database IDs

• PubChem SID: 162254785
• PubChem CID: 71313412

CALCULATED PROPERTIES

• Acid pKa: 3.8615007
• H Acceptors: 14
• H Donor: 5
• LogD (pH = 5.5): 0.7677895
• LogD (pH = 7.4): 0.74025434
• Log P: 0.7723393
• Molar Refractivity: 193.7949 cm^3
• Polarizability: 77.885635 Å^3
• Polar Surface Area: 193.91 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A637745

seco 10,11-Anhydro Clarithromycin is a forced degradation product of Clarithromycin (C559750).

REFERENCES

• Itai, S. et al.: Kag. Ryo. Ryoik., 7, 1531 (1991)