(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

• ChemBase ID: 1156
• Molecular Formular: C42H69NO15
• Molecular Mass: 827.99496
• Monoisotopic Mass: 827.46672051
• SMILES: O([C@H]1[C@H](N(C)C)[C@@H](O)[C@@H](O[C@@H]1C)O[C@H]1[C@H](C[C@H]([C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)C)[C@@H]1OC)C)C)CC=O)[C@@H]1O[C@H]([C@H](OC(=O)CC(C)C)[C@](O)(C1)C)C
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)[C@@H](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)OC(=O)CC(C)C)OC)OC(=O)C)C
• InChI: InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
• InChIKey: XJSFLOJWULLJQS-NGVXBBESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
• IUPAC Traditional name: josamycin
• Brand Name: Josacine; Kitasamycin A3; Turimycin A5
• Synonyms: Leucomycin A3; JM; Antibiotic yl-704 A3; Josamicina [inn-spanish]; Josamycine [inn-french]; Josamycinum [inn-latin]; Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate); Leucomycin V, 3-acetate 4(sup beta)-(3-methylbutanoate); Leucomycin V, 3-acetate 4B-(3-methylbutanoate); Josamycin; 3-Acetate 4B-(3-methylbutanoate)leucomycin V; Antibiotic YL 704A3; EN 141; Iosalide; Jomybel; Josacine; Josamina; Josamycin; Kitasamycin A3; Turimycin A5; Vilprafen; Wilprafen; Leucomycin A3

Database IDs

• CAS Number: 16846-24-5
• PubChem SID: 46505431; 160964619
• PubChem CID: 5282165

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.6682625
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 0.852045
• LogD (pH = 7.4): 2.6009817
• Log P: 3.216376
• Molar Refractivity: 211.0335 cm^3
• Polarizability: 84.798904 Å^3
• Polar Surface Area: 206.05 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.47
• LOG S: -4.19
• Solubility (Water): 5.35e-02 g/l

DETAILS

DrugBank - DB01321

• Drug Groups: approved
• Description: A macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens. [PubChem]
• Indication: For the treatment of bacterial infections.
• Pharmacology: Josamycin is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.
• Affected Organisms: Enteric bacteria and other eubacteria
• References: Przybylski P, Pyta K, Stefanska J, Brzezinski B, Bartl F: Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin. Magn Reson Chem. 2010 Apr;48(4):286-96. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - L330310

A 16-membered ring macrolide antibiotic with antimicrobial activity against a wide range of pathogens. Particularly used in the treatment of Mycoplasma infection.

REFERENCES

• Przybylski P, Pyta K, Stefanska J, Brzezinski B, Bartl F: Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin. Magn Reson Chem. 2010 Apr;48(4):286-96. Pubmed
• Osono, T. et al.: J. Antibiot., 27, 366 (1974)
• Kuriaki, K. et al.: Jpn. J. Antibiot., 22, 232 (1974)
• Tan K. et al.: Zhonghua Yiyuamganranxue Zazhi, 16, 235 (1974)