(3S,4R,5R,6S,7S,9S,12R,14S)-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; octadecanoic acid

• ChemBase ID: 133139
• Molecular Formular: C55H103NO15
• Molecular Mass: 1018.40402
• Monoisotopic Mass: 1017.7327716
• SMILES: CCCCCCCCCCCCCCCCCC(=O)O.CC[C@H]1C([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: CC[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)[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.CCCCCCCCCCCCCCCCCC(=O)O
• InChI: InChI=1S/C37H67NO13.C18H36O2/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;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2-17H2,1H3,(H,19,20)/t18-,19+,20?,21+,22-,23-,24-,25-,26-,28+,29+,30+,31-,32-,34-,35-,36+,37?;/m0./s1
• InChIKey: YAVZHCFFUATPRK-JGJPHTNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S,7S,9S,12R,14S)-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; octadecanoic acid
• IUPAC Traditional name: (3S,4R,5R,6S,7S,9S,12R,14S)-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; stearic acid
• Synonyms: Erythromycin stearate

Database IDs

• CAS Number: 643-22-1
• EC Number: 211-396-1
• MDL Number: MFCD00084690
• PubChem SID: 24894693; 162227416
• PubChem CID: 16219336

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: 23
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: KF5785000
• 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
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - E9256

Application
Erythromycin stearate is used to study leucocyte motility and transformation and on release in vitro of prostaglandin E2 by stimulated leucocytes1. It is also used to study abnormal polymorphonuclear leucocyte migration and chemotaxis2,3.
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).