2-[(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}-4-hydroxy-5-methoxy-9,16-dimethyl-10-{[(5S,6R)-6-methyl-5-[(2H3)methyl(methyl)amino]oxan-2-yl]oxy}-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

• ChemBase ID: 177852
• Molecular Formular: C43H74N2O14
• Molecular Mass: 843.05266
• Monoisotopic Mass: 842.51400506
• 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)O
• 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)O)C)OC1CC[C@@H]([C@H](O1)C)N(C)C
• InChI: InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34?,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1
• InChIKey: ACTOXUHEUCPTEW-PAHZGSOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(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}-4-hydroxy-5-methoxy-9,16-dimethyl-10-{[(5S,6R)-6-methyl-5-[(^2H₃)methyl(methyl)amino]oxan-2-yl]oxy}-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• IUPAC Traditional name: 2-[(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}-4-hydroxy-5-methoxy-9,16-dimethyl-10-{[(5S,6R)-6-methyl-5-[(^2H₃)methyl(methyl)amino]oxan-2-yl]oxy}-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• Synonyms: 9-O-[(2R,5S,6R)-5-(Dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]leucomycin V-d3; Foromacidin A-d3; Spiramycin A-d3; Spiramycin I-d3

Database IDs

• PubChem SID: 164233762
• PubChem CID: 71752231

CALCULATED PROPERTIES

• Acid pKa: 12.505557
• H Acceptors: 15
• H Donor: 4
• LogD (pH = 5.5): -3.1795146
• LogD (pH = 7.4): 0.02314118
• Log P: 2.4961133
• Molar Refractivity: 219.2458 cm^3
• Polarizability: 87.86806 Å^3
• Polar Surface Area: 195.38 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Off-White Solid
• Melting Point: 123-126°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Temperature and Moisture Sensitive

DETAILS

Toronto Research Chemicals - S682302

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)