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

• ChemBase ID: 174624
• Molecular Formular: C41H67NO15
• Molecular Mass: 813.96838
• Monoisotopic Mass: 813.45107045
• SMILES: O1C(=O)C[C@H]([C@@H]([C@H]([C@H](C[C@H]([C@H](/C=C/C=C/C[C@H]1C)O)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)OC(=O)CC)C)N(C)C)O)OC)OC(=O)CC
• 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)OC)OC(=O)CC)C
• InChI: InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1
• InChIKey: DMUAPQTXSSNEDD-QALJCMCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propanoyloxy)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl propanoate
• IUPAC Traditional name: midecamycin
• Synonyms: Leucomycin V 3,4B-Dipropanoate; Aboren; Antibiotic SF 837; Antibiotic SF 837A1; Antibiotic YL 704B1; Espinomycin A; Macropen; Medecamycin A1; Medemycin; Medemycin A1; Midecamycin A1; Midecin; Momicine; Mydecamycin; Mydecamycin A1; Myoxam; NSC 154011; Normicina; Platenomycin B1; Rubimycin; SF 837; SF 837A1; Turimycin P3; YL 704B1; Midecamycin

Database IDs

• CAS Number: 35457-80-8
• PubChem SID: 164230534
• PubChem CID: 5282169

CALCULATED PROPERTIES

• Acid pKa: 12.6682625
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 0.82099307
• LogD (pH = 7.4): 2.5699298
• Log P: 3.1853242
• Molar Refractivity: 206.5108 cm^3
• Polarizability: 82.96867 Å^3
• Polar Surface Area: 206.05 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M343250

A 16-membered ring macrolide antibiotic used in ophthalmology as well as other medical fields.

REFERENCES

• Matsui, K. et al.: J. Inter. Cytokin Res., 24, 197 (2004)
• Schmalreck, A.F. et al.: Antiinfect Drugs Chemother., 14, 225 (2004)
• Tokuda, H. et al.: Chemother., 21, 887 (2004)