CHEBI:70710 - eribulin mesylate

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ChEBI Name eribulin mesylate
ChEBI ID CHEBI:70710
Definition A methanesulfonate salt obtained by reaction of eribulin with one equivalent of methanesulfonic acid. A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C41H63NO14S
Net Charge 0
Average Mass 826.00200
Monoisotopic Mass 825.39693
InChI InChI=1S/C40H59NO11.CH4O3S/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;1-5(2,3)4/h19,23-39,43H,2-3,5-18,41H2,1,4H3;1H3,(H,2,3,4)/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+;/m1./s1
InChIKey QAMYWGZHLCQOOJ-WRNBYXCMSA-N
SMILES CS(O)(=O)=O.[H][C@@]12CC[C@]3([H])O[C@@]([H])(CC[C@@]45C[C@]6([H])O[C@]7([H])[C@@]([H])(O[C@@]8([H])CC[C@]([H])(CC(=O)C[C@]9([H])[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@@]9([H])C[C@@]([H])(O1)C(=C)[C@H](C)C2)O[C@]8([H])[C@]7([H])O4)[C@H]6O5)CC3=C
Roles Classification
Biological Role(s): microtubule-destabilising agent
Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing eribulin mesylate (CHEBI:70710) has part eribulin(1+) (CHEBI:70711)
eribulin mesylate (CHEBI:70710) has role antineoplastic agent (CHEBI:35610)
eribulin mesylate (CHEBI:70710) has role microtubule-destabilising agent (CHEBI:61951)
eribulin mesylate (CHEBI:70710) is a methanesulfonate salt (CHEBI:38037)
IUPAC Name
2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy-7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3'-5,6)pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4H)-one methanesulfonate
Synonyms Sources
E 7389 ChemIDplus
E7389 ChemIDplus
Eribulin mesilate KEGG DRUG
Brand Name Source
Halaven KEGG DRUG
Manual Xref Database
D08914 KEGG DRUG
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Registry Numbers Types Sources
11271529 Reaxys Registry Number Reaxys
441045-17-6 CAS Registry Number ChemIDplus
441045-17-6 CAS Registry Number KEGG DRUG
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Last Modified
19 October 2012