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 antibacterial [1-2,4].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Edlund C, Sillerström E, Wahlund E, Nord CE. (1998)
In vitro activity of HMR 3647 against anaerobic bacteria.
J Chemother, 10 (4): 280-4. [PMID:9720465]
2. Goldstein EJ, Citron DM, Hunt Gerardo S, Hudspeth M, Merriam CV. (1998)
Activities of HMR 3004 (RU 64004) and HMR 3647 (RU 66647) compared to those of erythromycin, azithromycin, clarithromycin, roxithromycin, and eight other antimicrobial agents against unusual aerobic and anaerobic human and animal bite pathogens isolated from skin and soft tissue infections in humans.
Antimicrob Agents Chemother, 42 (5): 1127-32. [PMID:9593139]
3. Makgatho M, Maimela E, Mbajiorgu F. (2015)
Ketolide agents HMR 3004 and HMR 3647 (telithromycin) inhibit the growth of Plasmodium falciparum in vitro.
Afr Health Sci, 15 (4): 1271-6. [PMID:26958030]
4. Malathum K, Coque TM, Singh KV, Murray BE. (1999)
In vitro activities of two ketolides, HMR 3647 and HMR 3004, against gram-positive bacteria.
Antimicrob Agents Chemother, 43 (4): 930-6. [PMID:10103202]