erythromycin   

GtoPdb Ligand ID: 1456

Abbreviated name: EM-A
Synonyms: E-Mycin® | Erythrocin® | erythromycin-A
erythromycin is an approved drug (FDA (no history prior to 1964))
Comment: Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 193.91
Molecular weight 733.46
XLogP 1.14
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCC1OC(=O)C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(CC(C(=O)C(C(C1(C)O)O)C)C)(C)O
Isomeric 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
InChI Key ULGZDMOVFRHVEP-RWJQBGPGSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (no history prior to 1964))
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
International Nonproprietary Names
INN number INN
39 erythromycin
Synonyms
E-Mycin® | Erythrocin® | erythromycin-A
Database Links
BindingDB Ligand 50344942
BitterDB Ligand 99
CAS Registry No. 114-07-8 (source: ChEBI)
ChEBI CHEBI:42355
ChEMBL Ligand CHEMBL532
DrugBank Ligand DB00199
DrugCentral Ligand 1048
GtoPdb PubChem SID 135652682
PubChem CID 12560
RCSB PDB Ligand ERY
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Search UniChem for chemical match using the InChIKey ULGZDMOVFRHVEP-RWJQBGPGSA-N
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Wikipedia Erythromycin