(dodecyloxy)sulfonic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-6-methyloxan-3-yl propanoate

• ChemBase ID: 168176
• Molecular Formular: C52H97NO18S
• Molecular Mass: 1056.38748
• Monoisotopic Mass: 1055.64263627
• SMILES: [C@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](C(=O)[C@@H]([C@H]1O)C)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)OC(=O)CC)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(C)O.CCCCCCCCCCCCOS(=O)(=O)O
• Canonical SMILES: CCC(=O)O[C@H]1[C@@H](O[C@@H](C[C@H]1N(C)C)C)O[C@@H]1[C@@H](C)[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@@H](C)C(=O)O[C@H](CC)[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]1(C)O)C)C)O)(C)O.CCCCCCCCCCCCOS(=O)(=O)O
• InChI: InChI=1S/C40H71NO14.C12H26O4S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3;2-12H2,1H3,(H,13,14,15)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-;/m1./s1
• InChIKey: AWMFUEJKWXESNL-JZBHMOKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (dodecyloxy)sulfonic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-{[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-6-methyloxan-3-yl propanoate
• IUPAC Traditional name: N-dodecyl sulfate erythromycin propionate
• Synonyms: Erythromycin 2'-propanoate Dodecyl Sulfate Salt; Erythromycin Estolate

Database IDs

• CAS Number: 3521-62-8
• PubChem SID: 162262308
• PubChem CID: 441371

CALCULATED PROPERTIES

• Acid pKa: 12.66394
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 1.3999294
• LogD (pH = 7.4): 3.1439457
• Log P: 3.7380502
• Molar Refractivity: 199.8155 cm^3
• Polarizability: 81.44333 Å^3
• Polar Surface Area: 199.98 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Alcohol; Chloroform; Water (0.024 mg/ml),
• Apperance: Long Needles
• Melting Point: 135-140°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E650000

Used as an antibacterial agent. LD50 >5000 mg/kg for oral administration to rats.

REFERENCES

• Goldenthal, E.I.: Toxicol. Appl. Pharmacol., 18, 185 (1971)