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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2D Structure
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Physico-chemical Properties
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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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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
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Wikipedia Eribulin