CHEBI:63587 - eribulin

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ChEBI Name eribulin
ChEBI ID CHEBI:63587
Definition 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.
Submitter Anonymous
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Formula C40H59NO11
Net Charge 0
Average Mass 729.89660
Monoisotopic Mass 729.409
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
InChIKey UFNVPOGXISZXJD-JBQZKEIOSA-N
SMILES [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 (CHEBI:63587) has role antineoplastic agent (CHEBI:35610)
eribulin (CHEBI:63587) has role microtubule-destabilising agent (CHEBI:61951)
eribulin (CHEBI:63587) is a cyclic ketal (CHEBI:59779)
eribulin (CHEBI:63587) is a cyclic ketone (CHEBI:3992)
eribulin (CHEBI:63587) is a macrocycle (CHEBI:51026)
eribulin (CHEBI:63587) is a polycyclic ether (CHEBI:36468)
eribulin (CHEBI:63587) is a polyether (CHEBI:46774)
eribulin (CHEBI:63587) is a primary amino compound (CHEBI:50994)
eribulin (CHEBI:63587) is conjugate base of eribulin(1+) (CHEBI:70711)
Incoming eribulin(1+) (CHEBI:70711) is conjugate acid of eribulin (CHEBI:63587)
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
Synonym Source
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one IUPAC
Database Links Databases
4171 DrugCentral
Eribulin Wikipedia
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Registry Numbers Types Sources
253128-41-5 CAS Registry Number ChemIDplus
9893060 Reaxys Registry Number Reaxys
Last Modified
22 February 2017