telithromycin   Click here for help

GtoPdb Ligand ID: 10878

Synonyms: HMR-3647 | Ketek® | Levviax® | RU-66647 | RU66647
Approved drug
telithromycin is an approved drug (EMA (2001), FDA (2004))
Compound class: Synthetic organic
Comment: Telithromycin is a ketolide antibiotic [1-2,4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 171.85
Molecular weight 811.47
XLogP 3.03
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@H]1OC(=O)[C@H](C)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]2[C@]1(C)OC(=O)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)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]2[C@]1(C)OC(=O)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
InChI InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37+,38-,40+,42-,43-/m1/s1
InChI Key LJVAJPDWBABPEJ-XZVSULPPSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2001), FDA (2004))
Withdrawn drug? Yes
IUPAC Name Click here for help
(1S,2R,5R,7R,8R,9R,11R,13R,14S)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
International Nonproprietary Names Click here for help
INN number INN
7803 telithromycin
Synonyms Click here for help
HMR-3647 | Ketek® | Levviax® | RU-66647 | RU66647
Database Links Click here for help
CAS Registry No. 191114-48-4 (source: PubChem)
GtoPdb PubChem SID 405560319
PubChem CID 11693521
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