(2R,3R,6R,7S,8S,9R)-3-[(2R,3S)-2,3-dihydroxypentan-2-yl]-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,6,8,10,12-pentamethyl-4,13-dioxabicyclo[8.2.1]tridec-1(12)-en-5-one

• ChemBase ID: 177095
• Molecular Formular: C37H65NO12
• Molecular Mass: 715.9115
• Monoisotopic Mass: 715.45067653
• SMILES: [C@@]([C@@H](CC)O)(C)(O)[C@H]1[C@H](C2=C(CC([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)(O2)C)C)C
• Canonical SMILES: CC[C@H]([C@]([C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@@H]([C@H](C2(OC(=C(C)C2)[C@@H]1C)C)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)N(C)C)C)(O)C)O
• InChI: InChI=1S/C37H65NO12/c1-14-25(39)37(10,43)32-20(4)28-18(2)16-36(9,50-28)31(49-34-27(40)24(38(11)12)15-19(3)45-34)21(5)29(22(6)33(42)48-32)47-26-17-35(8,44-13)30(41)23(7)46-26/h19-27,29-32,34,39-41,43H,14-17H2,1-13H3/t19-,20+,21+,22-,23+,24+,25+,26+,27-,29+,30+,31-,32-,34+,35-,36?,37-/m1/s1
• InChIKey: NMIWBQUQCOMGHJ-NFDOVYCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,6R,7S,8S,9R)-3-[(2R,3S)-2,3-dihydroxypentan-2-yl]-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,6,8,10,12-pentamethyl-4,13-dioxabicyclo[8.2.1]tridec-1(12)-en-5-one
• IUPAC Traditional name: (2R,3R,6R,7S,8S,9R)-3-[(2R,3S)-2,3-dihydroxypentan-2-yl]-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-2,6,8,10,12-pentamethyl-4,13-dioxabicyclo[8.2.1]tridec-1(12)-en-5-one
• Synonyms: (2R,3R,6R,7S,8S,9R,10R)-7-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-3-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-2,6,8,10,12-pentamethyl-9-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-4,13-dioxabicyclo[8.2.1]tridec-12-en-5-one; 8,9-Anhydropseudo-erythromycin A-6,9-hemiketal; EM 701; LY 267108; Pseudo Erythromycin A Enol Ether

Database IDs

• CAS Number: 105882-69-7
• PubChem SID: 164233005
• PubChem CID: 71751870

CALCULATED PROPERTIES

• Acid pKa: 12.482889
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -0.6122356
• LogD (pH = 7.4): 0.9426148
• Log P: 2.6263459
• Molar Refractivity: 184.7083 cm^3
• Polarizability: 74.75085 Å^3
• Polar Surface Area: 165.84 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 116-121°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P839500

Erythromycin impurity.

REFERENCES

• Lartey, P.A., et al.: Advan. Pharmacol., 28, 307 (1994)
• Tonini, M., et al.: Pharmacol. Res., 33, 217 (1994)