GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

fidaxomicin   Click here for help

GtoPdb Ligand ID: 10909

Synonyms: Dificid® | Dificlir® | lipiarmycin | OPT-80 | PAR-101 | tiacumicin B
Approved drug PDB Ligand
fidaxomicin is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Fidaxomicin is a narrow-spectrum, semisynthetic, macrolide antibacterial. It was isolated from the hamdenensis subspecies of actinomycete Dactylosporangium aurantiacum.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 16
Hydrogen bond donors 7
Rotatable bonds 15
Topological polar surface area 266.66
Molecular weight 1056.43
XLogP 5.76
No. Lipinski's rules broken 4

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
Click here for help

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/)

✖
Canonical SMILES CO[C@@H]1[C@H](OC/C/2=C\C=C\C[C@H](O)/C(=C/[C@H](CC)[C@H](/C(=C/C(=C/C[C@H](OC2=O)[C@H](O)C)/C)/C)O[C@@H]2OC(C)(C)[C@H]([C@@H]([C@@H]2O)O)OC(=O)C(C)C)/C)O[C@@H]([C@H]([C@@H]1O)OC(=O)c1c(O)c(Cl)c(c(c1CC)Cl)O)C
Isomeric SMILES CO[C@@H]1[C@H](OC/C/2=C\C=C\C[C@H](O)/C(=C/[C@H](CC)[C@H](/C(=C/C(=C/C[C@H](OC2=O)[C@H](O)C)/C)/C)O[C@@H]2OC(C)(C)[C@H]([C@@H]([C@@H]2O)O)OC(=O)C(C)C)/C)O[C@@H]([C@H]([C@@H]1O)OC(=O)c1c(O)c(Cl)c(c(c1CC)Cl)O)C
InChI InChI=1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)42(61)44(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)43(30)70-50-41(60)40(59)46(52(10,11)72-50)71-47(62)24(3)4/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17+/t28-,29-,30+,33+,34+,40-,41+,42+,43+,44-,45+,46+,50-,51-/m1/s1
InChI Key ZVGNESXIJDCBKN-UUEYKCAUSA-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. EU EMA (2011)  |  US FDA (2011)
International Nonproprietary Names Click here for help
INN number INN
9038 fidaxomicin
Synonyms Click here for help
Dificid® | Dificlir® | lipiarmycin | OPT-80 | PAR-101 | tiacumicin B
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Fidaxomicin
Other databases
CAS Registry No. 873857-62-6 (source: PubChem)
ChEMBL Ligand CHEMBL1255800
DrugBank Ligand DB08874
DrugCentral Ligand 4180
GtoPdb PubChem SID 405560350
PubChem CID 10034073
RCSB PDB Ligand FI8
Search Google for chemical match using the InChIKey ZVGNESXIJDCBKN-UUEYKCAUSA-N
Search Google for chemicals with the same backbone ZVGNESXIJDCBKN
Search PubMed clinical trials fidaxomicin
Search PubMed titles fidaxomicin
Search PubMed titles/abstracts fidaxomicin
UniChem Compound Search for chemical match using the InChIKey ZVGNESXIJDCBKN-UUEYKCAUSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZVGNESXIJDCBKN-UUEYKCAUSA-N