eribulin   Click here for help

GtoPdb Ligand ID: 6813

Synonyms: E7389 | ER 086526 | Halaven® | NSC-707389
Approved drug PDB Ligand
eribulin is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: A pan tubulin inhibitor which is a fully synthetic macrocyclic ketone analogue of the marine sponge natural product halichondrin B (a mitosis inhibitor). Marketed formulations may contain eribulin mesylate (PubChem CID 17755248).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: eribulin

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 12
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 146.39
Molecular weight 729.41
XLogP 0.56
No. Lipinski's rules broken 1
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 NCC(CC1OC2C(C1OC)CC(=O)CC1CCC3C(O1)C1OC4(CCC5OC(CCC6OC(C2)C(=C)C(C6)C)C(=C)C5)OC2C(O3)C1OC2C4)O
Isomeric SMILES NC[C@H](C[C@H]1O[C@@H]2[C@@H]([C@H]1OC)CC(=O)C[C@H]1CC[C@H]3[C@H](O1)[C@@H]1O[C@]4(CC[C@@H]5O[C@@H](CC[C@@H]6O[C@H](C2)C(=C)[C@@H](C6)C)C(=C)C5)O[C@@H]2[C@H](O3)[C@H]1O[C@@H]2C4)O
InChI InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
InChI Key UFNVPOGXISZXJD-JBQZKEIOSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2011))
International Nonproprietary Names Click here for help
INN number INN
8854 eribulin
Synonyms Click here for help
E7389 | ER 086526 | Halaven® | NSC-707389
Database Links Click here for help
CAS Registry No. 253128-41-5
ChEBI CHEBI:63587
ChEMBL Ligand CHEMBL1683590
DrugBank Ligand DB08871
DrugCentral Ligand 4171
GtoPdb PubChem SID 178103419
PubChem CID 11354606
RCSB PDB Ligand 6K9
Search Google for chemical match using the InChIKey UFNVPOGXISZXJD-JBQZKEIOSA-N
Search Google for chemicals with the same backbone UFNVPOGXISZXJD
Search PubMed clinical trials eribulin
Search PubMed titles eribulin
Search PubMed titles/abstracts eribulin
UniChem Compound Search for chemical match using the InChIKey UFNVPOGXISZXJD-JBQZKEIOSA-N
UniChem Connectivity Search for chemical match using the InChIKey UFNVPOGXISZXJD-JBQZKEIOSA-N
Wikipedia Eribulin