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CHEBI:177413 - plinabulin

Default Structure
ChEBI IDCHEBI:177413
ChEBI Nameplinabulin
Stars
DefinitionA member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione substituted by benzylidene and (5-tert-butyl-1H-imidazol-4-yl)methylidene groups at positions 3 and 6, respectively. It is a vascular disrupting agent and a microtubule destabalising agent which was in clinical trials (now discontinued) for the treatment of non-small cell lung cancer.
Last Modified8 June 2022
SubmitterMetaboLights
DownloadsMolfile
FormulaC19H20N4O2
Net Charge0
Average Mass336.395
Monoisotopic Mass336.15863
SMILESCC(C)(C)c1ncnc1/C=c1\nc(=O)/c(=C/c2ccccc2)nc1=O
InChIInChI=1S/C19H20N4O2/c1-19(2,3)16-13(20-11-21-16)10-15-18(25)22-14(17(24)23-15)9-12-7-5-4-6-8-12/h4-11H,1-3H3,(H,20,21)(H,22,25)(H,23,24)/b14-9-,15-10-
InChIKeyUNRCMCRRFYFGFX-TYPNBTCFSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Sus scrofa (ncbitaxon:9823) sausage (ENVO:00002166) MetaboLights (MTBLS2871)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
microtubule-destabilising agent  Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
plinabulin (CHEBI:177413) has role angiogenesis inhibitor (CHEBI:48422)
plinabulin (CHEBI:177413) has role antineoplastic agent (CHEBI:35610)
plinabulin (CHEBI:177413) has role apoptosis inducer (CHEBI:68495)
plinabulin (CHEBI:177413) has role microtubule-destabilising agent (CHEBI:61951)
plinabulin (CHEBI:177413) is a 2,5-diketopiperazines (CHEBI:65061)
plinabulin (CHEBI:177413) is a benzenes (CHEBI:22712)
plinabulin (CHEBI:177413) is a imidazoles (CHEBI:24780)
plinabulin (CHEBI:177413) is a olefinic compound (CHEBI:78840)
IUPAC Name 
(3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
INNs  Source
plinabulinWHO MedNet
plinabulinaWHO MedNet
plinabulineWHO MedNet
plinabulinumWHO MedNet
Synonyms  Source
BPI 2358ChEBI
BPI-2358ChEBI
NPI 2358ChemIDplus
NPI-2358ChemIDplus
NPI2358ChEBI
Manual XrefsDatabases
8125252ChemSpider
D09655KEGG DRUG
DB05992DrugBank
LSM-43250LINCS
PlinabulinWikipedia
PN6PDBeChem
Registry NumbersSources
CAS:714272-27-2ChemIDplus
Citations