(4R,5S,6S,7R,9R,11E,13E,16R)-6-{[(2R,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl acetate

• ChemBase ID: 179373
• Molecular Formular: C48H79NO18
• Molecular Mass: 958.13676
• Monoisotopic Mass: 957.52971469
• SMILES: [C@@H]1(OC(=O)C[C@H]([C@@H]([C@H]([C@H](C[C@H](C(=O)/C=C/C(=C/C1CO[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1OC)OC)O)C)/C)C)CC=O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C)O[C@@H]1O[C@@H]([C@@H]([C@@](C1)(O)C)O)C)N(C)C)O)C)OC(=O)C)CC
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)C(=O)/C=C/C(=C/C([C@H](OC(=O)C[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)N(C)C)O[C@@H]1O[C@H](C)[C@@H]([C@](C1)(C)O)O)C)OC(=O)C)CC)CO[C@@H]1O[C@@H](C)[C@H]([C@H]([C@@H]1OC)OC)O)/C
• InChI: InChI=1S/C48H79NO18/c1-14-34-32(23-60-47-44(59-13)43(58-12)39(54)27(5)62-47)19-24(2)15-16-33(52)25(3)20-31(17-18-50)41(26(4)35(64-30(8)51)21-36(53)65-34)67-46-40(55)38(49(10)11)42(28(6)63-46)66-37-22-48(9,57)45(56)29(7)61-37/h15-16,18-19,25-29,31-32,34-35,37-47,54-57H,14,17,20-23H2,1-13H3/b16-15+,24-19+/t25-,26+,27-,28-,29+,31+,32?,34-,35-,37+,38-,39-,40-,41-,42-,43-,44-,45+,46+,47-,48-/m1/s1
• InChIKey: SXJMWODQOMKONK-AXZSYZCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S,7R,9R,11E,13E,16R)-6-{[(2R,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl acetate
• IUPAC Traditional name: (4R,5S,6S,7R,9R,11E,13E,16R)-6-{[(2R,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl acetate
• Synonyms: 3-O-Acetyltylosin; Tylosin 3-Acetate

Database IDs

• CAS Number: 63409-10-9
• PubChem SID: 164235283
• PubChem CID: 71752879

CALCULATED PROPERTIES

• Acid pKa: 12.439671
• H Acceptors: 17
• H Donor: 4
• LogD (pH = 5.5): 1.0597552
• LogD (pH = 7.4): 2.5464554
• Log P: 2.7570326
• Molar Refractivity: 241.3586 cm^3
• Polarizability: 97.19206 Å^3
• Polar Surface Area: 244.74 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T947660

A new acyl derivative of Tylosin (T947650) produced by microbial transformation.

REFERENCES

• Okamoto, R., et al.: J. Antibiotics, 33, 1300 (1980)