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

• ChemBase ID: 159452
• Molecular Formular: C45H76N2O15
• Molecular Mass: 885.08934
• Monoisotopic Mass: 884.52456974
• 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)OC1CC[C@@H]([C@H](O1)C)N(C)C)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)O)C)N(C)C)O)OC)OC(=O)C
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)[C@H](/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]1C[C@@](C)(O)[C@H]([C@H](O1)C)O)OC)OC(=O)C)C)OC1CC[C@@H]([C@H](O1)C)N(C)C
• InChI: InChI=1S/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27-,28-,29+,31+,32+,33+,34-,36?,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1
• InChIKey: ZPCCSZFPOXBNDL-ZJFYXNKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl acetate
• IUPAC Traditional name: (4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl acetate
• Synonyms: 9-O-[(2R,5S,6R)-5-(Dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-3-acetate-leucomycin V; Foromacidin B; Spiramycin II; Acetyl Spiramycin

Database IDs

• CAS Number: 24916-51-6
• PubChem SID: 162253587
• PubChem CID: 60148896

CALCULATED PROPERTIES

• Acid pKa: 12.52555
• H Acceptors: 15
• H Donor: 3
• LogD (pH = 5.5): -2.7383893
• LogD (pH = 7.4): 0.46426666
• Log P: 2.9372387
• Molar Refractivity: 228.3973 cm^3
• Polarizability: 91.71757 Å^3
• Polar Surface Area: 201.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 130-133°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A187800

Antibiotic substance classified in the erythromycin-carbomycin group.

REFERENCES

• Sous, H., et al.: Arzneim.-Forsch., 8, 386 (1958)
• Mitscher, et al.: J. Antibiot., 26, 55 (1973)