ammonium 2-[(2R,3S,4S,5S,6S)-6-[(1S)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-3-{[(2R,4S,5R,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy}-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetate

• ChemBase ID: 172471
• Molecular Formular: C47H83NO17
• Molecular Mass: 934.15842
• Monoisotopic Mass: 933.5661002
• SMILES: C1C[C@@]2(O[C@@]1([C@H]1CC[C@](O1)([C@H]1[C@H](C[C@@H](O1)[C@H]1O[C@@]([C@@H](C[C@@H]1C)C)(O)C)O[C@H]1O[C@H]([C@H]([C@H](C1)OC)OC)C)C)C)C[C@@H]([C@H]([C@H](O2)[C@@H]([C@H]1[C@H]([C@H]([C@@H]([C@](O1)(CC(=O)[O-])O)C)OC)OC)C)C)O.[NH4+]
• Canonical SMILES: CO[C@H]1C[C@H](O[C@H]([C@H]1OC)C)O[C@H]1C[C@@H](O[C@H]1[C@]1(C)CC[C@@H](O1)[C@]1(C)CC[C@@]2(O1)C[C@H](O)[C@H]([C@H](O2)[C@@H]([C@@H]1O[C@](O)(CC(=O)[O-])[C@H]([C@@H]([C@@H]1OC)OC)C)C)C)[C@H]1O[C@](C)(O)[C@@H](C[C@@H]1C)C.[NH4+]
• InChI: InChI=1S/C47H80O17.H3N/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50;/h23-33,35-42,48,51-52H,14-22H2,1-13H3,(H,49,50);1H3/t23-,24+,25+,26-,27-,28-,29-,30-,31+,32-,33+,35+,36-,37-,38-,39-,40+,41+,42+,43-,44-,45-,46+,47+;/m0./s1
• InChIKey: WQGJEAMPBSZCIF-YZXWOGHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium 2-[(2R,3S,4S,5S,6S)-6-[(1S)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-3-{[(2R,4S,5R,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy}-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetate
• IUPAC Traditional name: ammonium 2-[(2R,3S,4S,5S,6S)-6-[(1S)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-3-{[(2R,4S,5R,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy}-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetate
• Synonyms: Cygro; Maduramicin Ammonium; Maduramycin Ammonium; Maduramicin α, Monoammonium Salt; Prinicin Ammonium; CL 259971; Maduramicin

Database IDs

• CAS Number: 84878-61-5
• PubChem SID: 164228381
• PubChem CID: 71749872

CALCULATED PROPERTIES

• Acid pKa: 4.0074344
• H Acceptors: 17
• H Donor: 3
• LogD (pH = 5.5): 3.2711616
• LogD (pH = 7.4): 1.6186899
• Log P: 4.7735076
• Molar Refractivity: 238.1188 cm^3
• Polarizability: 92.997665 Å^3
• Polar Surface Area: 211.58 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 173-176 °C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M110000

Polyether antibiotic chemically related to the lonomycins. Coccidiostat.

REFERENCES

• Liu, C.-M., et al.: J. Antibiot., 36, 343 (1983)
• Boxall, A., et al.: Toxicol. Lett., 131, 19 (1983)
• Campagnolo, E., et al.: Sci. Total Environ., 299, 89 (1983)
• Kreuzig, R., et al.: Environ. Toxicol Chem., 24, 777 (1983)