(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-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}-10-({[2-(2H3)methoxy(2H4)ethoxy]methoxy}imino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one

• ChemBase ID: 177479
• Molecular Formular: C41H76N2O15
• Molecular Mass: 837.04654
• Monoisotopic Mass: 836.52456974
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](/C(=N\OCOCCOC)/[C@@H]([C@H]1O)C)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)(O)C
• Canonical SMILES: COCCOCO/N=C/1\[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
• InChIKey: RXZBMPWDPOLZGW-XMRMVWPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-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}-10-({[2-(^2H₃)methoxy(^2H₄)ethoxy]methoxy}imino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-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}-10-({[2-(^2H₃)methoxy(^2H₄)ethoxy]methoxy}imino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• Synonyms: (9E)-9-[O-[(2-Methoxyethoxy-d7)methyl]oxime] Erythromycin; Assoral-d7; Brilid-d7; Claramid-d7; Forilin-d7; Overal-d7; RU 28965-d7; RU 965-d7; Rossitrol-7; Rotramin-d7; Roxeptin-d7; Roxid-d7; Roxithromycin-d7; Roxithromycin A-d7; Rulid-d7; Surlid-d7; Roxithromycin-d7

Database IDs

• PubChem SID: 164233389
• PubChem CID: 71752044

CALCULATED PROPERTIES

• H Donor: 5
• LogD (pH = 5.5): -0.23886713
• LogD (pH = 7.4): 1.3162447
• Log P: 2.9999793
• Molar Refractivity: 211.2376 cm^3
• Polarizability: 85.90249 Å^3
• Polar Surface Area: 216.89 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• Acid pKa: 12.454023
• H Acceptors: 16

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 113-118°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R700852

Semisynthetic labelled Erythromycin derivative. Antibacterial.

REFERENCES

• Jones, R.N., et al.: Antimicrob. Agents Chemother., 24, 209 (1983)
• Barry, A.L., et al.: Eur. J. Clin. Microbiol., 5, 536 (1983)
• Grassi, C., et al.: Chemioterapia, 6, 41 (1983)