(3S,4R,5R,6S,7S,9S,12R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-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-1-oxacyclotetradecane-2,10-dione; (dodecyloxy)sulfonic acid

• ChemBase ID: 132682
• Molecular Formular: C49H93NO17S
• Molecular Mass: 1000.32422
• Monoisotopic Mass: 999.61642152
• SMILES: CCCCCCCCCCCCOS(=O)(=O)O.CCC1C([C@@H](C(C(=O)[C@H](C[C@]([C@H]([C@@H]([C@H]([C@@H](C(=O)O1)C)O[C@H]1C[C@@]([C@H]([C@@H](O1)C)O)(C)OC)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)(C)O)C)C)O)(C)O
• Canonical SMILES: CCC1OC(=O)[C@@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@@H](C)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C[C@@H](C(=O)C([C@H](C1(C)O)O)C)C)(C)O.CCCCCCCCCCCCOS(=O)(=O)O
• InChI: InChI=1S/C37H67NO13.C12H26O4S/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2-12H2,1H3,(H,13,14,15)/t18-,19+,20?,21+,22-,23-,24-,25?,26-,28+,29+,30+,31-,32-,34-,35-,36+,37?;/m0./s1
• InChIKey: SKDGGFHGLZBNBC-NIMBSKFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S,7S,9S,12R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-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-1-oxacyclotetradecane-2,10-dione; (dodecyloxy)sulfonic acid
• IUPAC Traditional name: (3S,4R,5R,6S,7S,9S,12R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-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-1-oxacyclotetradecane-2,10-dione N-dodecyl sulfate
• Synonyms: Erythromycin 2′-propionate dodecyl sulfate; Erythromycin estolate

Database IDs

• CAS Number: 3521-62-8
• EC Number: 222-532-4
• MDL Number: MFCD00084691
• PubChem SID: 162226959; 24894679
• PubChem CID: 16219330

CALCULATED PROPERTIES

• Acid pKa: 12.438841
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.1920999
• LogD (pH = 7.4): 1.5732646
• Log P: 2.5963888
• Molar Refractivity: 186.0371 cm^3
• Polarizability: 75.76136 Å^3
• Polar Surface Area: 193.91 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42/43
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311

DETAILS

Sigma Aldrich - E8630

Application
Erythoromycin estolate is used to study hepatic cytochrome P-450 induction and inactivation via cytochrome-metabolite complex formation1 and Giardia intestinalis inefections2. It is used to study antibiotic cytotoxicity in cultured human liver cell lines3.
Biochem/physiol Actions
Erythromycin inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site) by binding to the 50s subunit of the bacterial 70s rRNA complex.
Erythromycin inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site).