Structure Database (LMSD)

Common Name
Erythromycin
Systematic Name
Synonyms
LM ID
LMPK04000006
Formula
Exact Mass
Calculate m/z
733.461244
Status
Curated




Classification

Biological Context

Erythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains.1 It is active against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l).2 Erythromycin (10-40 mg/kg) dose-dependently inhibits the growth of S. aureus in a mouse model of thigh infection.3 It also inhibits the cytochrome P450 (CYP450) isoform CYP3A4 in vitro with IC50 values of 33 and 27.3 µM for α-hydroxytriazolam and 4-hydroxytriazolam formation, respectively, following administration of triazolam, which is known to be metabolized primarily by CYP3A4.4,5 Formulations containing erythromycin have been used in the treatment of bacterial respiratory and skin infections, pertussis, and a variety of other bacterial infections.

This information has been provided by Cayman Chemical

References

2. Hoogeterp, J.J., Mattie, H., and van Furth, R. Activity of erythromycin and clindamycin in an experimental Staphylococcus aureus infection in normal and granulocytopenic mice. A comparative in vivo and in vitro study. Scand. J. Infect. Dis. 25(1), 123-132 (1993).
4. Kanatani, M.S., and Guglielmo, B.J. The new macrolides. Azithromycin and clarithromycin. Western J. Med. 160(1), 31-37 (1994).
5. Wilson, D.N. The A-Z of bacterial translation inhibitors. Crit. Rev. Biochem. Mol. Biol. 44(6), 393-433 (2009).

String Representations

InChiKey (Click to copy)
ULGZDMOVFRHVEP-RWJQBGPGSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@H]1(O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2O)C)[C@@H](C)[C@@H]([C@@H](C)C(=O)O[C@@H]([C@](O)(C)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)O)CC)O[C@@H]1O[C@H]([C@H](O)[C@](C)(OC)C1)C

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 51
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 731.57
Topological Polar Surface Area 200.12
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 14
logP 5.80
Molar Refractivity 193.43

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Updated at
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