clarithromycin   Click here for help

GtoPdb Ligand ID: 10903

Synonyms: 6-O-methylerythromycin | A-56268 | ABBOTT-56268 | Biaxin® | Klaricid® | TE-031
Approved drug PDB Ligand
clarithromycin is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Clarithromycin is a semisynthetic macrolide antibiotic. Structurally it is the 6-O-methyl ether of erythromycin A.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 182.91
Molecular weight 747.48
XLogP 1.66
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@@H](O2)C)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)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@@H](O2)C)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)OC
InChI InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI Key AGOYDEPGAOXOCK-KCBOHYOISA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1991))
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-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
International Nonproprietary Names Click here for help
INN number INN
6252 clarithromycin
Synonyms Click here for help
6-O-methylerythromycin | A-56268 | ABBOTT-56268 | Biaxin® | Klaricid® | TE-031
Database Links Click here for help
BindingDB Ligand 50404044
ChEMBL Ligand CHEMBL1741
DrugBank Ligand DB01211
GtoPdb PubChem SID 405560344
PubChem CID 84029
RCSB PDB Ligand CTY
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