(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-[(propylamino)methyl]oxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one

• ChemBase ID: 179283
• Molecular Formular: C41H79N3O12
• Molecular Mass: 806.07886
• Monoisotopic Mass: 805.56637498
• SMILES: [C@H]1(C[C@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O[C@@H]([C@]([C@@H]([C@H](NC1)C)O)(O)C)CC)C)O[C@@H]1O[C@@H]([C@@]([C@](C1)(C)OC)(O)CNCCC)C)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)(O)C)C
• Canonical SMILES: CCCNC[C@]1(O)[C@@H](C)O[C@H](C[C@@]1(C)OC)O[C@@H]1[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@H](NC[C@@H](C[C@@]([C@@H]([C@H]1C)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)N(C)C)(C)O)C)C
• InChI: InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1
• InChIKey: GUARTUJKFNAVIK-QPTWMBCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-[(propylamino)methyl]oxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one
• IUPAC Traditional name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-[(propylamino)methyl]oxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-Dideoxy-3-C-methyl-3-O-methyl-4-C-[(propylamino)methyl]-α-L-ribo-hexopyranosyl]oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one; CP 472295; Draxxin; Tulathromycin; Tulathromycin A

Database IDs

• CAS Number: 217500-96-4
• PubChem SID: 164235193
• PubChem CID: 9832301

CALCULATED PROPERTIES

• Acid pKa: 12.204279
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -7.152602
• LogD (pH = 7.4): -3.9605722
• Log P: 2.5004294
• Molar Refractivity: 210.7001 cm^3
• Polarizability: 86.03824 Å^3
• Polar Surface Area: 200.9 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 180-183°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T897150

Triamilide antibiotic for treatment of bovine and porcine respiratory disease. Exists as an equilibrium mixture of two isomeric forms, Tulathromycin A (90%) and B (10%). Antibacterial.

REFERENCES

• Benchaoui, H.A., et al.: J. Vet. Pharmacol. Ther., 27, 203 (2004)
• Nowakowski, M.A., et al.: Vet. Ther., 5, 60 (2004)