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

• ChemBase ID: 166635
• Molecular Formular: C39H65NO14
• Molecular Mass: 771.9317
• Monoisotopic Mass: 771.44050577
• SMILES: [C@@H]1(OC(=O)C[C@H]([C@@H]([C@H]([C@H](C[C@H](C(=O)/C=C/C(=C/[C@@H]1CO[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)N(C)C)O)C)O)CC
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)C(=O)/C=C/C(=C/[C@@H]([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)O)CC)CO[C@@H]1O[C@@H](C)[C@H]([C@H]([C@@H]1OC)OC)O)/C
• InChI: InChI=1S/C39H65NO14/c1-11-29-26(19-50-39-37(49-10)36(48-9)33(46)24(6)52-39)16-20(2)12-13-27(42)21(3)17-25(14-15-41)35(22(4)28(43)18-30(44)53-29)54-38-34(47)31(40(7)8)32(45)23(5)51-38/h12-13,15-16,21-26,28-29,31-39,43,45-47H,11,14,17-19H2,1-10H3/b13-12+,20-16+/t21-,22+,23-,24-,25+,26-,28-,29-,31+,32-,33-,34-,35-,36-,37-,38+,39-/m1/s1
• InChIKey: QRPHLEPFYLNRDA-NLGRAQRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-{[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-4-hydroxy-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• IUPAC Traditional name: 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-{[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-4-hydroxy-15-({[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy}methyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• Synonyms: 4A-O-De(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)tylosin; Demycarosyltylosin; Tylosin B; Desmycosin

Database IDs

• CAS Number: 11032-98-7
• PubChem SID: 162260768
• PubChem CID: 6437804

CALCULATED PROPERTIES

• Acid pKa: 12.528803
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 0.12036979
• LogD (pH = 7.4): 1.6312355
• Log P: 1.8586183
• Molar Refractivity: 198.21 cm^3
• Polarizability: 79.11693 Å^3
• Polar Surface Area: 199.98 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D296870

Desmycosin is a 16-membered macrolide antibiotic and a metabolite of Tylosin (T947650). Desmycosin is also a precursor to Tilmicosin (T440500).

REFERENCES

• Wal, J.M. et al.: J. Antibiot., 26, 687 (1973)
• Hu, D. et al.: Environ. Toxicol. Chem., 26, 884 (1973)
• Min, Y. et al.: Proc. Biochem., 42, 729 (1973)