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CHEBI:63587 - eribulin

ChEBI IDCHEBI:63587
ChEBI Nameeribulin
Stars
DefinitionA 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
Last Modified22 February 2017
DownloadsMolfile
FormulaC40H59NO11
Net Charge0
Average Mass729.908
Monoisotopic Mass729.40881
SMILES[H][C@@]12CC[C@]3([H])O[C@@]4([H])[C@H]5O[C@]6(CC[C@@]7([H])CC(=C)[C@]([H])(CC[C@@]8([H])C[C@@H](C)C(=C)[C@@]([H])(C[C@]9([H])O[C@H](C[C@H](O)CN)[C@H](OC)[C@@]9([H])CC(=O)C1)O8)O7)C[C@@]5([H])O[C@@]4([H])[C@@]([H])(O6)[C@@]3([H])O2
InChIInChI=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
InChIKeyUFNVPOGXISZXJD-JBQZKEIOSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
microtubule-destabilising agent  Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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-oneIUPAC
Manual XrefsDatabases
EribulinWikipedia
4171DrugCentral
Registry NumbersSources
Reaxys:9893060Reaxys
CAS:253128-41-5ChemIDplus