(2R,3S,4S,5R,6R,8R,10R,11R,12R,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6,11,12,13-tetrahydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,6,8,10,12-hexamethyl-9-oxopentadecanoic acid

• ChemBase ID: 168173
• Molecular Formular: C37H69NO14
• Molecular Mass: 751.94206
• Monoisotopic Mass: 751.47180589
• SMILES: [C@]([C@@H](CC)O)([C@@H]([C@H](C(=O)[C@@H](C[C@]([C@@H]([C@H]([C@@H]([C@@H](C)C(=O)O)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)(O)C)C)C)O)(O)C
• Canonical SMILES: CC[C@H]([C@]([C@@H]([C@H](C(=O)[C@@H](C[C@]([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)(O)C)C)C)O)(O)C)O
• InChI: InChI=1S/C37H69NO14/c1-14-25(39)37(10,47)30(42)20(4)27(40)18(2)16-35(8,46)32(52-34-28(41)24(38(11)12)15-19(3)49-34)21(5)29(22(6)33(44)45)51-26-17-36(9,48-13)31(43)23(7)50-26/h18-26,28-32,34,39,41-43,46-47H,14-17H2,1-13H3,(H,44,45)/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: HFOWQTSULPOIHU-RWJQBGPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R,8R,10R,11R,12R,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6,11,12,13-tetrahydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,6,8,10,12-hexamethyl-9-oxopentadecanoic acid
• IUPAC Traditional name: (2R,3S,4S,5R,6R,8R,10R,11R,12R,13R)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6,11,12,13-tetrahydroxy-3-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,6,8,10,12-hexamethyl-9-oxopentadecanoic acid
• Synonyms: Erythromycin Hydrolyzed Metabolite; [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12R*,13R*)]-3-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]pentadecanoic Acid; seco Erythromycin

Database IDs

• CAS Number: 143416-84-6
• PubChem SID: 162262305
• PubChem CID: 71316416

CALCULATED PROPERTIES

• Acid pKa: 3.811162
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -0.80049896
• LogD (pH = 7.4): -0.8289018
• Log P: -0.7965528
• Molar Refractivity: 189.5293 cm^3
• Polarizability: 76.89474 Å^3
• Polar Surface Area: 225.14 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E649960

A hydrolyzed metabolite of Erythromycin (E649950).

REFERENCES

• Barra, M. et al.: J. Chem. Res. Syn., 7, 220 (1992)