(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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

• ChemBase ID: 127295
• Molecular Formular: C37H67NO13
• Molecular Mass: 733.92678
• Monoisotopic Mass: 733.46124121
• SMILES: CC[C@H]1[C@@]([C@@H]([C@H](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@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
• InChI: InChI=1S/C37H67NO13/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/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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
• IUPAC Traditional name: erythromycin
• Brand Name: E-mycin, Erythrocin
• Synonyms: Erythromycin; Erythromycin; Erythromycinum; 红霉素; 红霉素

Database IDs

• CAS Number: 114-07-8
• EC Number: 204-040-1
• MDL Number: MFCD00084654
• Beilstein Number: 75279
• PubChem SID: 24869227; 24869225; 162221616; 24894661
• PubChem CID: 12560; 3255
• CHEBI ID: 42355
• ATC CODE: D10AF02; S01AA17; QJ51FA01; J01FA01
• CHEMBL: 532
• Chemspider ID: 12041
• DrugBank ID: DB00199
• IUPHAR ligand ID: 1456
• KEGG ID: D00140
• Unique Ingredient Identifier: 63937KV33D
• Wikipedia Title: Erythromycin
• Medline Plus: a682381

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: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble
• Melting Point: 133-135 °C
• Optical Rotation: [α]20/D -75±4°, c = 2% in ethanol

Safety Information

• RTECS: KF437500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: oral, iv, im, topical, ophthalmic eye drops
• Bioavailability: Depends on the ester type between 30% - 65%
• Excretion: bile
• Half Life: 1.5 hours
• Metabolism: liver (under 5% excreted unchanged)
• Protein Bound: 90%
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: A (Australia); B (US)
• Gene Information: human ... ABCB1(5243), CYP3A4(1576), MLNR(2862)mouse ... Abcb1a(18671), Abcb1b(18669)

Product Information

• Purity: ≥95.0% (NT)
• Grade: Biotechnology Performance Certified; Ph Eur
• Suitability: suitable for 1694 per US EPA
• Impurities: endotoxin, tested
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to BP 794; traceable to PhEur E1305000; traceable to USP 1242000
• Empirical Formula (Hill Notation): C37H67NO13

DETAILS

Sigma Aldrich - E7904

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step (aminoacyl translocation A-site to P-site). Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 45674

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site). Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

Sigma Aldrich - 16221

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.

Sigma Aldrich - 45673

Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Inhibits bacterial protein synthesis by binding to the ribosomes1; Inducible erythromycin resistance in bacteria2