telavancin   Click here for help

GtoPdb Ligand ID: 10925

Synonyms: TD-6424 | TD6424 | Vibativ®
Approved drug
telavancin is an approved drug (FDA (2009), EMA (2011))
Compound class: Synthetic organic
Comment: Telavancin is a glycopeptide antibacterial drug that is derived from vancomycin [1]. It is used to treat Gram-positive infections, including MRSA.
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 32
Hydrogen bond donors 23
Rotatable bonds 31
Topological polar surface area 607.9
Molecular weight 1753.64
XLogP 5.94
No. Lipinski's rules broken 4
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 CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c([C@H](NC2=O)C(=O)O)cc(c(c3O)CNCP(=O)(O)O)O)O)O[C@H]([C@H]1O)C
Isomeric SMILES CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c([C@H](NC2=O)C(=O)O)cc(c(c3O)CNCP(=O)(O)O)O)O)O[C@H]([C@H]1O)C
InChI InChI=1S/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1
InChI Key ONUMZHGUFYIKPM-MXNFEBESSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2009), EMA (2011))
Withdrawn drug? Yes
International Nonproprietary Names Click here for help
INN number INN
8504 telavancin
Synonyms Click here for help
TD-6424 | TD6424 | Vibativ®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Telavancin, TD-6424 (Vibrativ)
Other databases
CAS Registry No. 372151-71-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL507870
DrugBank Ligand DB06402
DrugCentral Ligand 4116
GtoPdb PubChem SID 405560366
PubChem CID 3081362
Search Google for chemical match using the InChIKey ONUMZHGUFYIKPM-MXNFEBESSA-N
Search Google for chemicals with the same backbone ONUMZHGUFYIKPM
Search PubMed clinical trials telavancin
Search PubMed titles telavancin
Search PubMed titles/abstracts telavancin
UniChem Compound Search for chemical match using the InChIKey ONUMZHGUFYIKPM-MXNFEBESSA-N
UniChem Connectivity Search for chemical match using the InChIKey ONUMZHGUFYIKPM-MXNFEBESSA-N