(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,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: 155901
• Molecular Formular: C42H69NO15
• Molecular Mass: 827.99496
• Monoisotopic Mass: 827.46672051
• SMILES: C[C@@H]1C/C=C\C=C\[C@@H]([C@@H](C[C@@H]([C@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C)O[C@H]1C[C@@]([C@H]([C@@H](O1)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
• 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/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
• InChIKey: XJSFLOJWULLJQS-XRUKWLHHSA-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,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: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,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
• Synonyms: Josamycin; Josamycin solution

Database IDs

• CAS Number: 16846-24-5
• EC Number: 231-791-2; 240-871-6
• MDL Number: MFCD00211043
• PubChem SID: 162250039; 24881768
• PubChem CID: 71312234

CALCULATED PROPERTIES

• 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

PROPERTIES

Safety Information

• German water hazard class: 2; nwg
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (UV)
• Concentration: 1 mg/mL in 1 mM EDTA
• Empirical Formula (Hill Notation): C42H69NO15

DETAILS

Sigma Aldrich - 59983

Application
Josamycin is used to study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.
Josamycin is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics, immunomodulatory effects , the suppression of matrix metalloproteinase production as well as study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.
Biochem/physiol Actions
Josamycin inhibits bacterial protein biosynthesis by inhibiting peptidyltransferase and ribosomal translocation, and depleting the intracellular pools of aminoacyl-tRNAs available for protein synthesis by drop-off and incomplete peptidyl-tRNA hydrolase activity. 1. Josamycin slows down formation of the first peptide bond of a nascent peptide in an amino acid-dependent way and inhibits formation of the second or third peptide bond 2.