4-(dimethylamino)-2-({14-ethyl-7,12,13-trihydroxy-4-[(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 1-ethyl butanedioate

• ChemBase ID: 105432
• Molecular Formular: C43H75NO16
• Molecular Mass: 862.0527
• Monoisotopic Mass: 861.50858533
• SMILES: CCOC(=O)CCC(=O)OC1C(CC(C)OC1OC1C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(=O)OC(CC)C(C)(O)C(O)C(C)C(=O)C(C)CC1(C)O)N(C)C
• Canonical SMILES: CCOC(=O)CCC(=O)OC1C(OC(CC1N(C)C)C)OC1C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C)C(=O)OC(CC)C(C(C(C(=O)C(CC1(C)O)C)C)O)(C)O
• InChI: InChI=1S/C43H75NO16/c1-15-29-43(11,52)36(48)24(5)33(47)22(3)20-41(9,51)38(25(6)34(26(7)39(50)57-29)59-32-21-42(10,53-14)37(49)27(8)56-32)60-40-35(28(44(12)13)19-23(4)55-40)58-31(46)18-17-30(45)54-16-2/h22-29,32,34-38,40,48-49,51-52H,15-21H2,1-14H3
• InChIKey: NSYZCCDSJNWWJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(dimethylamino)-2-({14-ethyl-7,12,13-trihydroxy-4-[(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 1-ethyl butanedioate
• IUPAC Traditional name: erythromycin ethylsuccinate
• Synonyms: Erythromycin ethyl succinate; ERYTHROMYCIN ETHYL SUCCINATE

Database IDs

• CAS Number: 1264-62-6
• EC Number: 215-033-8
• MDL Number: MFCD00084692
• PubChem SID: 24894684; 162092123
• PubChem CID: 3256

CALCULATED PROPERTIES

• Acid pKa: 12.66394
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 1.0269583
• LogD (pH = 7.4): 2.7709746
• Log P: 3.365079
• Molar Refractivity: 215.5996 cm^3
• Polarizability: 87.788155 Å^3
• Polar Surface Area: 226.28 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: WM9800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C43H75NO16

DETAILS

Sigma Aldrich - E8755

Application
Erythromycin ethyl succinate is used to study erythromycin-resistant Streptococcus pyogenes and Streptococcus pneumoniae1. It has been used to study down-regulation of motilin receptors on rabbit colon myocytes2 and lethal mutations in outer membrane genes omsA and firA in Salmonella typhimurium3.
Biochem/physiol Actions
Erythromycin ethyl succinate inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site).
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.