teicoplanin   Click here for help

GtoPdb Ligand ID: 10924

Synonyms: Antibiotic 8327A | MDL-507 | Targocid® | teichomycin | teicoplanin A2
Approved drug
teicoplanin is an approved drug (UK (1989))
Compound class: Synthetic organic
Comment: Teicoplanin is a glycopeptide antibacterial drug [4]. Its spectrum of activity similar to that of vancomycin, with activity against Gram-positive bacteria including Staphylococci and Clostridium spp.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 33
Hydrogen bond donors 24
Rotatable bonds 22
Topological polar surface area 662.41
Molecular weight 1877.56
XLogP 3.08
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCCC(=O)N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO)Oc1c2cc3cc1Oc1ccc(cc1Cl)C[C@@H]1C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]3C(=O)N[C@@H]([C@@H](c4ccc(O2)c(Cl)c4)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2NC(=O)C)O)O)C(=O)N[C@@H](c2c(c4cc3ccc4O)c(cc(c2)O)OC2O[C@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)C(=O)O)c2cc(O)cc(c2)Oc2cc([C@H](C(=O)N1)N)ccc2O
Isomeric SMILES CCCCCCCCCC(=O)N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO)Oc1c2cc3cc1Oc1ccc(cc1Cl)C[C@@H]1C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]3C(=O)N[C@@H]([C@@H](c4ccc(O2)c(Cl)c4)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2NC(=O)C)O)O)C(=O)N[C@@H](c2c(c4cc3ccc4O)c(cc(c2)O)OC2O[C@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)C(=O)O)c2cc(O)cc(c2)Oc2cc([C@H](C(=O)N1)N)ccc2O
InChI InChI=1S/C88H97Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/t48-,57-,58-,59-,62-,63-,64+,65-,66+,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88?/m1/s1
InChI Key BJNLLBUOHPVGFT-CAYRISATSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (1989))
International Nonproprietary Names Click here for help
INN number INN
5155 teicoplanin
Synonyms Click here for help
Antibiotic 8327A | MDL-507 | Targocid® | teichomycin | teicoplanin A2
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Teicoplanin
Reactome Drug Reactome logo R-ALL-9686880
Reactome Reaction Reactome logo R-HSA-9685655
Other databases
CAS Registry No. 61036-62-2 (source: WHO INN record)
DrugBank Ligand DB06149
GtoPdb PubChem SID 405560365
PubChem CID 133065662
Search Google for chemical match using the InChIKey BJNLLBUOHPVGFT-CAYRISATSA-N
Search Google for chemicals with the same backbone BJNLLBUOHPVGFT
Search PubMed clinical trials teicoplanin
Search PubMed titles teicoplanin
Search PubMed titles/abstracts teicoplanin
UniChem Compound Search for chemical match using the InChIKey BJNLLBUOHPVGFT-CAYRISATSA-N
UniChem Connectivity Search for chemical match using the InChIKey BJNLLBUOHPVGFT-CAYRISATSA-N