erythromycin   Click here for help

GtoPdb Ligand ID: 1456

Abbreviated name: EM-A
Synonyms: E-Mycin® | Erythrocin® | erythromycin-A
Approved drug PDB Ligand
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
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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
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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 Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (no history prior to 1964))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(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 Click here for help
INN number INN
39 erythromycin
Synonyms Click here for help
E-Mycin® | Erythrocin® | erythromycin-A
Database Links Click here for help
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 PubMed clinical trials erythromycin
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Search UniChem for chemical match using the InChIKey ULGZDMOVFRHVEP-RWJQBGPGSA-N
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Wikipedia Erythromycin