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

• ChemBase ID: 168180
• Molecular Formular: C37H70N2O12
• Molecular Mass: 734.9579
• Monoisotopic Mass: 734.49287569
• SMILES: [C@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H]([C@@H]([C@@H]([C@H]1O)C)N)C)(O)C)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)CC)(C)O
• 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@@H]([C@@H]([C@H]([C@]1(C)O)O)C)N)C)(C)O
• InChI: InChI=1S/C37H70N2O12/c1-14-25-37(10,45)30(41)20(4)27(38)18(2)16-35(8,44)32(51-34-28(40)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-32,34,40-42,44-45H,14-17,38H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: XCLJRCAJSCMIND-JCTYMORFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• Synonyms: (9S)-9-Amino-9-deoxoerythromycin; (9S)-9-Deoxy-9-aminoerythromycin A; (9S)-Erythromycylamine A; 9(S)-Erythromycylamine; BRL 42852ER; LY 024410; Erythromycylamine

Database IDs

• CAS Number: 26116-56-3
• PubChem SID: 162262312
• PubChem CID: 83952

CALCULATED PROPERTIES

• Acid pKa: 12.462311
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -4.4222364
• LogD (pH = 7.4): -1.9923238
• Log P: 1.8116286
• Molar Refractivity: 188.5721 cm^3
• Polarizability: 77.17386 Å^3
• Polar Surface Area: 202.86 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 123-127°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E653400

A metabolite of Dirithromycin; an antibiotic.

REFERENCES

• Bauldry, S., et al.: J. Biol. Chem., 263, 16787 (1988)
• Labro, M., et al.: J. Antimicrob. Chemother., 24, 561 (1988)
• Dumas, R., et al.: Chemother., 36, 381 (1988)
• Bacci, P., et al.: J. Chemother., 4, 268 (1988)