(2R,3R,4S,5R,8R,9S,10S,11R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-3,4-dihydroxy-9-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one

• ChemBase ID: 168174
• Molecular Formular: C37H65NO12
• Molecular Mass: 715.9115
• Monoisotopic Mass: 715.45067653
• SMILES: [C@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H](C2(CC(=C([C@@H]([C@H]1O)C)O2)C)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](C2(OC(=C(C)C2)[C@@H]([C@H]([C@]1(C)O)O)C)C)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)N(C)C
• InChI: InChI=1S/C37H65NO12/c1-14-25-37(10,43)30(40)20(4)28-18(2)16-36(9,50-28)32(49-34-27(39)24(38(11)12)15-19(3)45-34)21(5)29(22(6)33(42)47-25)48-26-17-35(8,44-13)31(41)23(7)46-26/h19-27,29-32,34,39-41,43H,14-17H2,1-13H3/t19-,20+,21+,22-,23+,24+,25-,26+,27-,29+,30-,31+,32-,34+,35-,36?,37-/m1/s1
• InChIKey: JFVYXJKGJMUGRG-MXTSOXSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,8R,9S,10S,11R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-3,4-dihydroxy-9-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one
• IUPAC Traditional name: (2R,3R,4S,5R,8R,9S,10S,11R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-3,4-dihydroxy-9-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one
• Synonyms: 11-(4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-ethyl-3,4-dihydroxy-9-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,4,8,10,12,14-hexamethyl-6,15-dioxa-bicyclo[10.2.1]pentadec-1(14)-en-7-one; Erythromycin A Enol Ether

Database IDs

• CAS Number: 33396-29-1
• PubChem SID: 162262306
• PubChem CID: 71316417

CALCULATED PROPERTIES

• Acid pKa: 12.464236
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -0.6122356
• LogD (pH = 7.4): 0.9426147
• Log P: 2.6263459
• Molar Refractivity: 184.7083 cm^3
• Polarizability: 74.75085 Å^3
• Polar Surface Area: 165.84 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 143-145°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E649970

Impurity E.

REFERENCES

• McGuire, J.M., et al.: Antibiot. Chemother., 6, 281 (1952)
• Steffansen, B., et al.: Int. J. Pharm., 56, 159 (1952)
• Goldman, R.C., et al.: Antimicrob. Agents Chemother., 34, 1973 (1952)